Composition for optical material

ABSTRACT

The composition for optical materials of the present invention comprises a compound having in one molecule at least one structure represented by the following formula (1): 
                 
 
wherein R 1 , R 2 , R 3 , R 4 , X, Y and n are as defined in the disclosure, an amine compound and an isocyanate compound. Resins obtained by curing the composition by polymerization are useful as well-balanced optical materials having a high impact resistance, a high refractive index and a sufficiently high Abbe&#39;s number.

TECHNICAL FIELD

The present invention relates to a resin composition suitable forproducing optical materials such as plastic lens, prism, optical fiber,information recording medium, and filter, particularly, for producing aplastic spectacle lens, and further relates to the optical materialproduced by curing the resin composition by polymerization.

BACKGROUND ART

Plastic materials are recently widely used in manufacturing opticalmaterials, particularly, spectacle lenses because of their light weight,toughness and easiness of dyeing. Optical materials, particularly,spectacle lenses are required to have a low specific gravity, a hightransparency, a low yellow degree, a high impact resistance, and opticalproperties such as a high refractive index and a high Abbe's number.

Polycarbonate known as optical materials having a high impact resistancehave some problems of (1) Abbe's number as low as 29, (2) ease ofcausing optical distortion, and (3) not so high refractive index as lowas 1.58, etc.

Japanese Patent Application Laid-Open No. 3-236386 discloses apolythiourethane compound derived from a polythiol compound and anisocyanate group-containing compound. Although higher in the refractiveindex, the proposed polythiourethane compound is lower thanpolycarbonates in the impact resistance.

“Latest Polyurethane Applied Technology”, CMC, pp89, 1983 discloses theproduction of a high-impact material by reacting a polyurethaneprepolymer, which is prepared from an OH-terminated polymer and adiisocyanate, with an active hydrogen compound such as amines andpolyols. The proposed material is higher in the impact resistance, butlower in the refractive index as compared with polycarbonates.

DISCLOSURE OF INVENTION

An object of the present invention is to provide well-balanced opticalmaterials having a high impact resistance, a high refractive index and asufficiently high Abbe's number, thereby decreasing the thickness of alens.

As a result of extensive study for achieving the object, the inventorshave found that a resin obtained by polymerizing a resin composition foroptical materials comprising a compound (hereinafter referred to as“compound (a)) having in one molecule at least one structure representedby the following formula (1):

wherein R¹ is a single bond or a C₁-C₁₀ hydrocarbon group; each of R²,R³ and R⁴ is a C₁-C₁₀ hydrocarbon group or hydrogen; X is S, O, Se orTe; Y is S, O, Se or Te; and n is an integer from 0 to 5,an amine compound (hereinafter referred to as “compound (b)), and anisocyanate compound (hereinafter referred to as “compound (c)) is awell-balanced optical material having a high impact resistance, a highrefractive index and a sufficiently high Abbe's number. The presentinvention has been accomplished on the basis of this finding.

Thus, in a first aspect of the present invention, there is provided acomposition for optical materials comprising a compound having in onemolecule at least one structure represented by the following formula(1):

wherein R¹ is a single bond or a C₁-C₁₀ hydrocarbon group; each of R²,R³ and R⁴ is a C₁-C₁₀ hydrocarbon group or hydrogen; X is S, O, Se orTe; Y is S, O, Se or Te; and n is an integer from 0 to 5,an amine compound, and an isocyanate compound.

In a second aspect of the present invention, there is provided anoptical material produced by curing the composition for opticalmaterials by polymerization.

BEST MODE FOR CARRYING OUT THE INVENTION

Each proportion of the compound (a), the compound (b) and the compound(c) in the composition for resin varies depending on the refractiveindex or viscosity of each compound and the properties of the resultingresin. Each proportion is preferably selected from respective ranges of0.5 to 90 parts by weight for the compound (a), 1 to 40 parts by weightfor the compound (b), and 10 to 90 parts by weight for compound (c). Ifexceeding the above ranges, a high impact resistance intended by thepresent invention is not achieved. In addition, there occur severaldisadvantages such as insufficient heat resistance, discoloration of thecured product and failure in achieving one of the objects of the presentinvention, i.e., a high refractive index and a high Abbe's number. Morepreferably, the compound (a) is 3 to 70 parts by weight, the compound(b) is 3 to 30 parts by weight and the compound (c) is 20 to 85 parts byweight. Most preferably, the compound (a) is 5 to 50 parts by weight,the compound (b) is 5 to 20 parts by weight and the compound (c) is 40to 80 parts by weight.

The Compound (a) includes compounds having in one molecule at least onestructure represented by the following formula (1):

wherein R¹, R², R³ R⁴, X, Y and n are defined as above.

To achieve well-balanced high refractive index and high Abbe's number,R¹ is preferably methylene or ethylene, and R², R³ and R⁴ are eachpreferably hydrogen or methyl. More preferably, R¹ is methylene, and R²,R³ and R⁴ are each hydrogen. The suffix n is an integer of 0 to 5,preferably an integer of 0 to 3, more preferably 1 or 2. X is S, O, Seor Te, preferably S, O or Se, and more preferably S or Se. Y is S, O, Seor Te, preferably S, O or Se, and more preferably S or Se.

The compound having in one molecule at least one structure representedby the formula (1) includes all organic compounds which meet such arequirement. A compound having in one molecule at least two structuresof the formula (1) is preferable. Preferred examples of the compoundshaving in one molecule at least one structure of the formula (1) are thefollowing epithio compounds (X═S). The episulfide compounds areclassified into (A) to (E), and described in detail below.

-   (A) Organic compound having at least one epithio group-   (B) Organic compound having at least one epithioalkyloxy group    (R¹=hydrocarbon group, X═S, Y═O, n=1)-   (C) Organic compound having at least one epithioalkylthio group    (R¹=hydrocarbon group, X═S, Y═S, n=1)-   (D) Organic compound having at least one epithioalkylseleno group    (R¹=hydrocarbon group, X═S, Y═Se, n=1)-   (E) Organic compound having at least one epithioalkyltelluro group    (R¹=hydrocarbon group, X═S, Y═Te, n=1)

In addition to the epithio structure, each episulfide compound (A), (B),(C), (D) and (E) described above has, as the main backbone, aliphaticchain backbone, aliphatic branched backbone, alicyclic backbone,aromatic backbone, or hetero cyclic backbone containing a hetero atomsuch as nitrogen, oxygen, sulfur, selenium, and tellurium. Theepisulfide compound may have two or more groups selected from epithiogroup, epithioalkyloxy group, epithioalkylthio group, epithioalkylselenogroup and epithioalkyltelluro group, simultaneously in one molecule.Further, these compounds may include linkage of sulfide, selenide,telluride, ether, sulfone, ketone, ester, amide, or urethane in themolecule.

Preferred examples of the episulfide compound (A) include compoundshaving an epoxy group (exclusive of glycidyl group) with its at leastone epoxy group replaced by epithio group. Examples are described below.

A-1: Organic Compounds having Aliphatic Chain Backbone

1,1-bis(epithioethyl)methane,1-(epithioethyl)-1-(β-epithiopropyl)methane,1,1-bis(β-epithiopropyl)methane,1-(epithioethyl)-1-(β-epithiopropyl)ethane,1,2-bis(β-epithiopropyl)ethane,1-(epithioethyl)-3-(β-epithiopropyl)butane,1,3-bis(β-epithiopropyl)propane,1-(epithioethyl)-4-(β-epithiopropyl)pentane,1,4-bis(β-epithiopropyl)butane,1-(epithioethyl)-5-(β-epithiopropyl)hexane,1-(epithioethyl)-2-(γ-epithiobutylthio)ethane,1-(epithioethyl)-2-[2-(γ-epithiobutylthio)ethylthio]ethane,tetrakis(β-epithiopropyl)methane, 1,1,1-tris(β-epithiopropyl)propane,1,3-bis(β-epithiopropyl)-1-(β-epithiopropyl)-2-thiapropane, and1,5-bis(β-epithiopropyl)-2,4-bis(β-epithiopropyl)-3-thiapentane;

A-2: Compounds having Alicyclic Backbone

1,3- or 1,4-bis(epithioethyl)cyclohexane, 1,3- or1,4-bis(β-epithiopropyl)cyclohexane,bis[4-(epithioethyl)cyclohexyl]methane,bis[4-(β-epithiopropyl)cyclohexyl]methane,2,2-bis[4-(epithioethyl)cyclohexyl]propane,2,2-bis[4-(β-epithiopropyl)cyclohexyl]propane,bis[4-(β-epithiopropyl)cyclohexyl] sulfide,bis[4-(epithioethyl)cyclohexyl] sulfide,2,5-bis(epithioethyl)-1,4-dithiane,2,5-bis(β-epithiopropyl)-1,4-dithiane, 4-epithioethyl-1,2-cyclohexenesulfide, 4-epoxy-1,2-cyclohexene sulfide, 2,3-, 2,5- or2,6-bis(1,2-epithioethyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(2,3-epithiopropyl)-1,4-diselenane, 2,4-, 2,5- or2,6-bis(1,2-epithioethyl)-1,3-diselenane, 2,4-, 2,5- or2,6-bis(2,4-epithiopropyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(1,2-epithioethyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(2,3-epithiopropyl)-1-thia-4-selenane, 2,4- or4,5-bis(1,2-epithioethyl)-1,3-diselenolane, 2,4- or4,5-bis(2,4-epithiopropyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(1,2-epithioethyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane, 2,3-, 2,4-, 2,5- or3,4-bis(1,2-epithioethyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(2,3-epithiopropyl)selenophane, 2,3-, 2,5-, or2,6-bis(1,2-epithioethyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(2,3-epithiopropyl)-1,4-ditellurane, 2,4-, 2,5- or2,6-bis(1,2-epithioethyl)-1,3-ditellurane, 2,4-, 2,5- or2,6-bis(2,4-epithiopropyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(1,2-epithioethyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or3,5-bis(2,3-epithiopropyl)-1-thia-4-tellurane, 2,4- or4,5-bis(1,2-epithioethyl)-1,3-ditellurolane, 2,4- or4,5-bis(2,4-epithiopropyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(1,2-epithioethyl) 1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(2,4-epithiopropyl)-1-thia-3-tellurolane, 2,3-, 2,4-, 2,5- or3,4-bis(1,2-epithioethyl)tellurophane, and 2,3-, 2,4-, 2,5- or3,4-bis(2,3-epithiopropyl)tellurophane;

A-3: Compounds having Aromatic Backbone

1,3- or 1,4-bis(epithioethyl)benzene, 1,3- or1,4-bis(β-epithiopropyl)benzene, bis[4-(epithioethyl)phenyl]methane,bis[4-(β-epithiopropyl)phenyl] methane,2,2-bis[4-(epithioethyl)phenyl]propane,2,2-bis[4-(β-epithiopropyl)phenyl]propane, bis[4-(epithioethyl)phenyl]sulfide, bis[4-(β-epithiopropyl)phenyl] sulfide,bis[4-(epithioethyl)phenyl] sulfone, bis[4-(β-epithiopropyl)phenyl]sulfone, 4,4′-bis(epithioethyl)biphenyl, and4,4′-bis(β-epithiopropyl)biphenyl; and

compounds obtained by replacing at least one hydrogen of the epithiogroup in the above compounds with methyl.

Preferred examples of the episulfide compound (B) include compoundsderived from an epihalohydrin, with its at least one glycidyl groupreplaced by epithioalkyloxy group (thioglycidyl group). Examples of theepoxy compounds include:

phenolic epoxy compounds prepared by condensing an epihalohydrin with apolyhydric phenol compounds such as hydroquinone, catechol, resorcinol,bisphenol A, bisphenol F, bisphenol sulfone, bisphenol ether, bisphenolsulfide, halogenated bisphenol A and novolak resins;

alcoholic epoxy compounds prepared by condensing an epihalohydrin with apolyhydric alcoholic compounds such as ethylene glycol, diethyleneglycol, triethylene glycol, polyethylene glycol, propylene glycol,dipropylene glycol, polypropylene glycol, 1,3-propanediol,1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerol,trimethylolpropane trimethacrylate, pentaerythritol, 1,3- or1,4-cyclohexanediol, 1,3- or 1,4-cyclohexanedimethanol,3-selenaheptane-1,5-diol, 2,5-bis(hydroxymethyl) selenophane,2,5-bis(4-hydroxy-2-selenabutyl) selenophane,2,6-dihydroxymethyl-1,4-diselenane,3,5-dihydroxymethyl-1-thia-4-selenane, 3-tellenaheptane-1,5-diol,2,5-bis(hydroxymethyl) tellurophane, 2,5-bis(4-hydroxy-2-tellenabutyl)tellurophane, 2,6-dihydroxymethyl-1,4-ditellurane,3,5-dihydroxymethyl-1-thia-4-tellurane, hydrogenated bisphenol A,bisphenol A/ethylene oxide adducts, and bisphenol A/propylene oxideadducts;

glycidyl ester epoxy compounds prepared by condensing an epihalohydrinwith a polybasic carboxylic acid such as adipic acid, sebacic acid,dodecandicarboxylic acid, dimer acid, phthalic acid, isoterephthalicacid, tetrahydrophthalic acid, methyltetrahydrophthalic acid,hexahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalicacid, HET acid, nadic acid, maleic acid, succinic acid, fumaric acid,trimellitic acid, benzenetetracarboxylic acid,benzophenonetetracarboxylic acid, naphthalenedicarboxylic acid anddiphenyldicarboxylic acid;

amine epoxy compounds prepared by condensing an epihalohydrin with aprimary diamine such as ethylenediamine, 1,2-diaminopropane,1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane,1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane,1,7-diaminoheptane, 1,8-diaminooctane, bis(3-aminopropyl) ether,1,2-bis(3-aminopropoxy)ethane,1,3-bis(3-aminopropoxy)-2,2′-dimethylpropane, 1,2-, 1,3- or1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane,hydrogenated 4,4′-diaminodiphenylmethane, isophoronediamine,1,4-bisaminopropylpiperadine, m- or p-phenylenediamine, 2,4- or2,6-tolylenediamine, n- or p-xylylenediamine, 1,5- or2,6-naphthalenediamine, 4,4′-diaminodiphenylmethane,4,4′-diaminodiphenyl ether and 2,2-(4,4′-diaminodiphenyl)propane;

amine epoxy compounds prepared by condensing an epihalohydrin with asecondary diamine such as N,N′-dimethylethylenediamine,N,N′-dimethyl-1,2-diaminopropane, N,N′-dimethyl-1,3-diaminopropane,N,N′-dimethyl-1,2-diaminobutane, N,N′-dimethyl-1,3-diaminobutane,N,N′-dimethyl-1,4-diaminobutane, N,N′-dimethyl-1,5-diaminopentane,N,N′-dimethyl-1,6-diaminohexane, N,N′-dimethyl-1,7-diaminoheptane,N,N′-diethylethylenediamine, N,N′-diethyl-1,2-diaminopropane,N,N′-diethyl-1,3-diaminopropane, N,N′-diethyl-1,2-diaminobutane,N,N′-diethyl-1,3-diaminobutane, N,N′-diethyl-1,4-diaminobutane,N,N′-diethyl-1,6-diaminohexane, piperadine, 2-methylpiperadine, 2,5- or2,6-dimethylpiperadine, homopiperadine, 1,1-di(4-piperidyl)methane,1,2-di(4-piperidyl)ethane, 1,3-di(4-piperidyl)propane, and1,4-di(4-piperidyl)butane; and

urethane epoxy compounds produced by the reaction of the abovepolyhydric alcohol compounds or phenol compounds with diisocyanatecompounds and glycidol.

Examples of the episulfide compound (B) are described below.

B-1: Organic Compounds having Aliphatic Chain Backbone

bis(β-epithiopropyl) ether, bis(β-epithiopropyloxy)methane,1,2-bis(β-epithiopropyloxy)ethane, 1,3-bis(β-epithiopropyloxy)propane,1,2-bis(β-epithiopropyloxy)propane,1-(β-epithiopropyloxy)-2-(β-epithiopropyloxymethyl)propane,1,4-bis(β-epithiopropyloxy)butane, 1,3-bis(β-epithiopropyloxy)butane,1-(β-epithiopropyloxy)-3-(β-epithiopropyloxymethyl)butane,1,5-bis(β-epithiopropyloxy)pentane,1-(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)pentane,1,6-bis(β-epithiopropyloxy)hexane,1-(β-epithiopropyloxy)-5-(β-epithiopropyloxymethyl)hexane,1-(β-epithiopropyloxy)-2-[(2-β-epithiopropyloxyethyl)oxy]ethane,1-(β-epithiopropyloxy)-2-[[2-(2-β-epithiopropyloxyethyl)oxyethyl]oxy]ethane,bis(5,6-epithio-3-oxahexyl) selenide, bis(5,6-epithio-3-oxahexyl)telluride, tetrakis(β-epithiopropyloxymethyl)methane,1,1,1-tris(β-epithiopropyloxymethyl)propane,1,5-bis(β-epithiopropyloxy)-2-(β-epithiopropyloxymethyl)-3-thiapentane,1,5-bis(β-epithiopropyloxy)-2,4-bis(β-epithiopropyloxymethyl)-3-thiapentane,1-(β-epithiopropyloxy)-2,2-bis(β-epithiopropyloxymethyl)-4-thiahexane,1,5,6-tris(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)-3-thiahexane,1,8-bis(β-epithiopropyloxy)-4-(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-4,5-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-4,4-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-2,4,5-tris(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyloxy)-2,5-bis(β-epithiopropyloxymethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropyloxy)-5-(β-epithiopropyloxymethyl)-5-[(2-β-epithiopropyloxyethyl)oxymethyl]-3,7-dithianonane,1,10-bis(β-epithiopropyloxy)-5,6-bis[(2-β-epithiopropyloxyethyl)oxy]-3,6,9-trithiadecane,1,11-bis(β-epithiopropyloxy)-4,8-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane,1,11-bis(P-epithiopropyloxy)-5,7-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyloxy)-5,7-[(2-β-epithiopropyloxyethyl)oxymethyl]-3,6,9-trithiaundecane,and1,11-bis(β-epithiopropyloxy)-4,7-bis(β-epithiopropyloxymethyl)-3,6,9-trithiaundecane;

B-2: Compounds having Alicyclic Backbone

1,3- or 1,4-bis(β-epithiopropyloxy)cyclohexane, 1,3- or1,4-bis(β-epithiopropyloxymethyl)cyclohexane,bis[4-(β-epithiopropyloxy)cyclohexyl]methane,2,2-bis[4-(β-epithiopropyloxy)cyclohexyl]propane,bis[4-(β-epithiopropyloxy)cyclohexyl] sulfide,2,5-bis(β-epithiopropyloxymethyl)-1,4-dithiane,2,5-bis(β-epithiopropyloxyethyloxymethyl)-1,4-dithiane, 2,4- or4,5-bis(3,4-epithio-1-oxabutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-oxapentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-selenolane,bis(3,4-epithio-1-oxabutyl)tricycloselenaoctane,bis(3,4-epithio-1-oxabutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-oxabutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-oxapentyl)selenophane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-oxapenyyl)-1,4-diselenane, 2,4-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,3-diselenane, 2,4-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-tellurolane,bis(3,4-epithio-1-oxabutyl)tricyclotelluraoctane,bis(3,4-epithio-1-oxabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-oxabutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epitho-2-oxapentyl)tellurophane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,4-ditellurane, 2,4-, 2,5- or2,6-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurane, 2,4-, 2,5- or2,6-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane, and 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane;

B-3: Compounds having Aromatic Backbone

1,3- or 1,4-bis(β-epithiopropyloxy)benzene, 1,3- or1,4-bis(β-epithiopropyloxymethyl)benzene,bis[4-(η-epithiopropyl)phenyl]methane,2,2-bis[4-(β-epithiopropylthio)phenyl]propane,bis[4-(β-epithiopropylthio)phenyl] sulfide,bis[4-(β-epithiopropylthio)phenyl] sulfone, and4,4′-bis(β-epithiopropylthio)biphenyl; and

compounds obtained by replacing at least one hydrogen of the epithiogroup in the above compounds with methyl.

Preferred examples of the episulfide compound (C) include epoxycompounds derived from a mercapto compound and an epihalohydrin, withits at least one epoxyalkylthio group (particularly, β-epoxypropylthiogroup) replaced by an epithioalkylthio group. Examples of the episulfidecompound (C) are described below.

C-1: Organic Compounds having Aliphatic Chain Backbone

bis(epithioethyl) sulfide, bis(epithioethyl) disulfide,bis(epithioethyl) trisulfide, bis(β-epithiopropyl) sulfide,bis(β-epithiopropyl) disulfide, bis(β-epithiopropyl) trisulfide,bis(β-epithiopropylthio)methane, 1,2-bis(β-epithiopropylthio)ethane,1,3-bis(β-epithiopropylthio)propane,1,2-bis(β-epithiopropylthio)propane,1-(β-epithiopropylthio)-2-(β-epithiopropylthiomethyl)propane,1,4-bis(β-epithiopropylthio)butane, 1,3-bis(β-epithiopropylthio)butane,1-(β-epithiopropylthio)-3-(β-epithiopropylthiomethyl)butane,1,5-bis(β-epithiopropylthio)pentane,1-(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)pentane,1,6-bis(β-epithiopropylthio)hexane,1-(β-epithiopropylthio)-5-(β-epithiopropylthiomethyl)hexane,1-(β-epithiopropylthio)-2-[(2-β-epithiopropylthioethyl)thio]ethane,1-(β-epithiopropylthio)-2-[[2-(2-β-epithiopropylthioethyl)thioethyl]thio]ethane,tetrakis(β-epithiopropylthiomethyl)methane,1,1,1-tris(β-epithiopropylthiomethyl)propane,1,5-bis(β-epithiopropylthio)-2-(β-epithiopropylthiomethyl)-3-thiapentane,1,5-bis(β-epithiopropylthio)-2,4-bis(β-epithiopropylthiomethyl)-3-thiapentane,1-(β-epithiopropylthio)-2,2-bis(β-epithiopropylthiomethyl)-4-thiahexane,1,5,6-tris(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)-3-thiahexane,1,8-bis(β-epithiopropylthio)-4-(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-4,5-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-4,4-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-2,4,5-tris(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylthio)-2,5-bis(β-epithiopropylthiomethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropylthio)-5-(β-epithiopropylthiomethyl)-5-[(2-β-epithiopropylthioethyl)thiomethyl]-3,7-dithianonane,1,10-bis(β-epithiopropylthio)-5,6-bis[(2-β-epithiopropylthioethyl)thio]-3,6,9-trithiadecane,1,11-bis(β-epithiopropylthio)-4,8-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylthio)-5,7-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylthio)-5,7-[(2-β-epithiopropylthioethyl)thiomethyl]-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylthio)-4,7-bis(β-epithiopropylthiomethyl)-3,6,9-trithiaundecane,tetra[2-(β-epithiopropylthio)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylthio)acetylmethyl]propane,tetra[2-(β-epithiopropylthiomethyl)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylthiomethyl)acetylmethyl]propane,bis(5,6-epithio-3-thiahexyl) selenide,2,3-bis(6,7-thioepoxy-1-selena-4-thiaheptyl)-1-(3,4-thioepoxy-1-thiabutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-thiapentyl)-2-selenapropane,bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy-1-thiabutyl),1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-thiaheptyl)butane,tris(4,5-thioepoxy-2-thiapentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-thiabutyl),bis(5,6-epithio-3-thiahexyl) telluride,2,3-bis(6,7-thioepoxy-1-tellura-4-thiaheptyl)-1-(3,4-thioepoxy-1-thiabutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-thiapentyl)-2-tellurapropane,bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thioepoxy-1-thiabutyl),1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-thiaheptyl)butane,andtris(4,5-thioepoxy-2-thiapentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-thiabutyl);

C-2: Compounds having Alicyclic Backbone

1,3- or 1,4-bis(β-epithiopropylthio)cyclohexane, 1,3- or1,4-bis(β-epithiopropylthiomethyl)cyclohexane,bis[4-(β-epithiopropylthio)cyclohexyl]methane,2,2-bis[4-(β-epithiopropylthio)cyclohexyl]propane,bis[4-(β-epithiopropylthio)cyclohexyl] sulfide,2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane,2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-thiabutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-thiapentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-thiabutyl)-1,3-diselenane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-thiapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or3,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio-1-thiabutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-thiapentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-selenolane,2,6-bis(4,5-epithio-2-thiapentyl)-1,3,5-triselenane,bis(3,4-epithio-1-thiabutyl)tricycloselenaoctane,bis(3,4-epithio-1-thiabutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-thiabutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-thiapentyl)selenophane,2-(4,5-thioepoxy-2-thiapentyl)-5-(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-epoxy-1-thiabutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-,2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-thiabutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or3,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane, 2,4- or4,5-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-tellurolane,2,6-bis(4,5-epithio-2-thiapentyl)-1,3,5-tritellurane,bis(3,4-epithio-1-thiabutyl)tricyclotelluraoctane,bis(3,4-epithio-1-thiabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-thiabutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-thiapentyl)tellurophane,2-(4,5-thioepoxy-2-thiapentyl)-5-(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane, and 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane;

C-3: Compounds having Aromatic Backbone

1,3- or 1,4-bis(β-epithiopropylthio)benzene, 1,3- or1,4-bis(β-epithiopropylthiomethyl)benzene,bis[4-(β-epithiopropylthio)phenyl]methane,2,2-bis[4-(β-epithiopropylthio)phenyl]propane,bis[4-(β-epithiopropylthio)phenyl] sulfide,bis[4-(β-epithiopropylthio)phenyl] sulfone, and4,4′-bis(β-epithiopropylthio)biphenyl; and

compounds obtained by replacing at least one hydrogen of theβ-epithiopropyl group in the above compounds with methyl.

Preferred examples of the episulfide compound (D) include epoxycompounds derived from an epihalohydrin and a selenium compound such asalkali metal selenide, alkali metal selenol, alkyl(aryl) selenol, andhydrogen selenide, with its at least one epoxyalkylseleno group(particularly, β-epoxypropylseleno group) replaced by anepithioalkylseleno group. Examples of the episulfide compounds (D) aredescribed below.

D-1: Organic Compounds having Aliphatic Chain Backbone

bis(epithioethly) selenide, bis(epithioethly) diselenide,bis(epithioethly) triselenide, bis(β-epithiopropyl) selenide,bis(β-epithiopropyl) diselenide, bis(β-epithiopropyl) triselenide,bis(β-epithiopropylseleno)methane, 1,2-bis(β-epithiopropylseleno)ethane,1,3-bis(β-epithiopropylseleno)propane,1,2-bis(β-epithiopropylseleno)propane,1-(β-epithiopropylseleno)-2-(β-epithiopropylselenomethyl)propane,1,4-bis(β-epithiopropylseleno)butane,1,3-bis(β-epithiopropylseleno)butane,1-(β-epithiopropylseleno)-3-(β-epithiopropylselenomethyl)butane,1,5-bis(β-epithiopropylseleno)pentane,1-(β-epithiopropylseleno)-4-(β-epithiopropylselenomethyl)pentane,1,6-bis(β-epithiopropylseleno)hexane,1-(β-epithiopropylseleno)-5-(β-epithiopropylselenomethyl)hexane,1-(β-epithiopropylseleno)-2-[(2-β-epithiopropylselenoethyl)thio]ethane,1-(β-epithiopropylseleno)-2-[[2-(2-β-epithiopropylselenoethyl)selenoethyl]thio]ethane,tetrakis(β-epithiopropylselenomethyl)methane,1,1,1-tris(β-epithiopropylselenomethyl)propane,1,5-bis(β-epithiopropylseleno)-2-(β-epithiopropylselenomethyl)-3-thiapentane,1,5-bis(β-epithiopropylseleno)-2,4-bis(β-epithiopropylselenomethyl)-3-thiapentane,1-(β-epithiopropylseleno)-2,2-bis(β-epithiopropylselenomethyl)-4-thiahexane,1,5,6-tris(β-epithiopropylseleno)-4-(β-epithiopropylselenomethyl)-3-thiahexane,1,8-bis(β-epithiopropylseleno)-4-(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-4,5-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-4,4-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-2,4,5-tris(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropylseleno)-2,5-bis(β-epithiopropylselenomethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropylseleno)-5-(β-epithiopropylselenomethyl)-5-[(2-β-epithiopropylselenoethyl)selenomethyl]-3,7-dithianonane,1,10-bis(β-epithiopropylseleno)-5,6-bis[(2-β-epithiopropylselenoethyl)thio]-3,6,9-trithiadecane,1,11-bis(β-epithiopropylseleno)-4,8-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-5,7-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-5,7-[(2-β-epithiopropylselenoethyl)selenomethyl]-3,6,9-trithiaundecane,1,11-bis(β-epithiopropylseleno)-4,7-bis(β-epithiopropylselenomethyl)-3,6,9-trithiaundecane,tetra[2-(β-epithiopropylseleno)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylseleno)acetylmethyl]propane,tetra[2-(β-epithiopropylselenomethyl)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropylselenomethyl)acetylmethyl]propane,bis(5,6-epithio-3-selenohexyl) selenide,2,3-bis(6,7-thioepoxy-1-selena-4-selenoheptyl)-1-(3,4-thioepoxy-1-selenobutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-selenopentyl)-2-selenapropane,bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy-1-selenobutyl),1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-selenoheptyl)butane,tris(4,5-thioepoxy-2-selenopentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-selenobutyl),bis(5,6-epithio-3-selenohexyl) telluride,2,3-bis(6,7-thioepoxy-1-tellura-4-selenoheptyl)-1-(3,4-thioepoxy-1-selenobutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-selenopentyl)-2-tellurapropane,bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thioepoxy-1-selenobutyl),1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-selenoheptyl)butane,andtris(4,5-thiepoxy-2-selenopentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-selenobutyl);

D-2: Compounds having Alicyclic Backbone

1,3- or 1,4-bis(β-epithiopropylseleno)cyclohexane, 1,3- or1,4-bis(β-epithiopropylselenomethyl)cyclohexane,bis[4-(β-epithiopropylseleno)cyclohexyl]methane,2,2-bis[4-(β-epithiopropylseleno)cyclohexyl]propane,bis[4-(β-epithiopropylseleno)cyclohexyl] sulfide,2,5-bis(β-epithiopropylselenomethyl)-1,4-dithiane,2,5-bis(β-epithiopropylselenoethylthiomethyl)-1,4-dithiane, 2,3-, 2,5-or 2,6-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane, 2,4- or4,5-bis(3,4-epithio-1-selenobutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-selenopentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-selenolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-selenolane,2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-triselenane,bis(3,4-epithio-1-selenobutyl)tricycloselenaoctane,bis(3,4-epithio-1-selenobutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-selenobutyl)selenophane, 2,3-, 2,4-, 2,5-,3,4-bis(4,5-epithio-2-selenopentyl)selenophane,2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-selenacyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-selenacyclohexane, 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-selenacyclohexane, 2,3-, 2,5- or2,6-bis(3,4-epithio-1-selenobutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-selenopentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-selenobutyl)-1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-tellurane, 2,4- or4,5-bis(3,4-epithio-1-selenobutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-telluroane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-tellurolane,2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-tritellurane,bis(3,4-epithio-1-selenobutyl)tricyclotelluraoctane,bis(3,4-epithio-1-selenobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-selenobutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-selenopentyl)tellurophane,2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-telluracyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-telluracyclohexane, and 2,3-,2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-telluracyclohexane;

D-3: Compounds having Aromatic Backbone

1,3- or 1,4-bis(β-epithiopropylseleno)benzene, 1,3- or1,4-bis(β-epithiopropylselenomethyl)benzene,bis[4-(β-epithiopropylseleno)phenyl]methane,2,2-bis[4-(β-epithiopropylseleno)phenyl]propane,bis[4-(β-epithiopropylseleno)phenyl] sulfide,bis[4-(β-epithiopropylseleno)phenyl] sulfone, and4,4′-bis(β-epithiopropylseleno)biphenyl; and

compounds obtained by replacing at least one hydrogen of theβ-epithiopropyl group in the above compounds with methyl.

Preferred examples of the episulfide compound (E) include epoxycompounds derived from an epihalohydrins and a tellurium compound suchas alkali metal telluride, alkali metal tellurol, alkyl(aryl) tellurol,and hydrogen telluride, with its at least one epoxyalkyltelluro group(particularly, β-epoxypropyltelluro group) replaced by anepithioalkyltelluro group. Examples of the episulfide compounds (E) aredescribed below.

E-1: Organic Compounds having Aliphatic Chain Backbone

bis(epithioethyl) telluride, bis(epithioethyl) ditelluride,bis(epithioethyl) tritelluride, bis(β-epithiopropyl) telluride,bis(β-epidithiopropyl) telluride, bis(β-epithiopropyl) ditelluride,bis(β-epidithiopropyl) ditelluride, bis(β-epithiopropyl) tritelluride,bis(β-epithiopropyltelluro)methane,1,2-bis(β-epithiopropyltelluro)ethane,1,3-bis(β-epithiopropyltelluro)propane,1,2-bis(β-epithiopropyltelluro)propane,1-(β-epithiopropyltelluro)-2-(β-epithiopropyltelluromethyl)propane,1,4-bis(β-epithiopropyltelluro)butane,1,3-bis(β-epithiopropyltelluro)butane,1-(β-epithiopropyltelluro)-3-(β-epithiopropyltelluromethyl)butane,1,5-bis(β-epithiopropyltelluro)pentane,1-(β-epithiopropyltelluro)-4-(β-epithiopropyltelluromethyl)pentane,1,6-bis(β-epithiopropyltelluro)hexane,1-(β-epithiopropyltelluro)-5-(β-epithiopropyltelluromethyl)hexane,1-(β-epithiopropyltelluro)-2-[(2-β-epithiopropyltelluroethyl)thio]ethane,1-(β-epithiopropyltelluro)-2-[[2-(2-β-epithiopropyltelluroethyl)telluroethyl]thio]ethane,tetrakis(β-epithiopropyltelluromethyl)methane,1,1,1-tris(β-epithiopropyltelluromethyl)propane,1,5-bis(β-epithiopropyltelluro)-2-(β-epithiopropyltelluromethyl)-3-thiapentane,1,5-bis(β-epithiopropyltelluro)-2,4-bis(β-epithiopropyltelluromethyl)-3-thiapentane,1-(β-epithiopropyltelluro)-2,2-bis(β-epithiopropyltelluromethyl)-4-thiahexane,1,5,6-tris(β-epithiopropyltelluro)-4-(β-epithiopropyltelluromethyl)-3-thiahexane,1,8-bis(β-epithiopropyltelluro)-4-(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyltelluro)-4,5-bis(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyltelluro)-4,4-bis(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyltelluro)-2,4,5-tris(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,8-bis(β-epithiopropyltelluro)-2,5-bis(β-epithiopropyltelluromethyl)-3,6-dithiaoctane,1,9-bis(β-epithiopropyltelluro)-5-(β-epithiopropyltelluromethyl)-5-[(2-β-epithiopropyltelluroethyl)selenomethyl]-3,7-dithianonane,1,10-bis(β-epithiopropyltelluro)-5,6-bis[(2-β-epithiopropyltelluroethyl)thio]-3,6,9-trithiadecane,1,11-bis(β-epithiopropyltelluro)-4,8-bis(β-epithiopropyltelluromethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyltelluro)-5,7-bis(β-epithiopropyltelluromethyl)-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyltelluro)-5,7-[(2-β-epithiopropyltelluroethyl)selenomethyl]-3,6,9-trithiaundecane,1,11-bis(β-epithiopropyltelluro)-4,7-bis(β-epithiopropyltelluromethyl)-3,6,9-trithiaundecane,tetra[2-(β-epithiopropyltelluro)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropyltelluro)acetylmethyl]propane,tetra[2-(β-epithiopropyltelluromethyl)acetylmethyl]methane,1,1,1-tri[2-(β-epithiopropyltelluromethyl)acetylmethyl]propane,bis(5,6-epithio-3-tellurohexyl) selenide,2,3-bis(6,7-thioepoxy-1-selena-4-telluroheptyl)-1-(3,4-thioepoxy-1-tellurobutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-telluropentyl)-2-selenapropane,bis(4,5-thioepoxy-2-telluropentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thioepoxy-1-tellurobutyl),1,4-bis(3,4-thioepoxy-1-tellurobutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-telluroheptyl)butane,tris(4,5-thioepoxy-2-telluropentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-tellurobutyl),bis(5,6-epithio-3-tellurohexyl) telluride,2,3-bis(6,7-thioepoxy-1-tellura-4-telluroheptyl)-1-(3,4-thioepoxy-1-tellurobutyl)propane,1,1,3,3-tetrakis(4,5-thioepoxy-2-telluropentyl)-2-tellurapropane,bis(4,5-thioepoxy-2-telluropentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thioepoxy-1-tellurobutyl),1,4-bis(3,4-thioepoxy-1-tellurobutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-telluroheptyl)butane,andtris(4,5-thiepoxy-2-telluropentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-tellurobutyl);

E-2 : Compounds having Alicyclic Backbone

1,3- or 1,4-bis(β-epithiopropyltelluro)cyclohexane, 1,3- or1,4-bis(β-epithiopropyltelluromethyl)cyclohexane,bis[4-(β-epithiopropyltelluro)cyclohexyl]methane,2,2-bis[4-(β-epithiopropyltelluro)cyclohexyl]propane,bis[4-(β-epithiopropyltelluro)cyclohexyl] sulfide,2,5-bis(β-epithiopropyltelluromethyl)-1,4-dithiane,2,5-bis(β-epithiopropyltelluroethylthiomethyl)-1,4-dithiane, 2,3-, 2,5-or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-diselenane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-telluropentyl)-1,4-diselenane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-telluropentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6-or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-selenolane, 2,4- or4,5-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenolane, 2,4- or4,5-bis(4,5-epithio-2-telluropentyl)-1,3-diselenolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-3-selenoolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-telluropentyl)-1-thia-3-selenolane,2,6-bis(4,5-epithio-2-telluropentyl)-1,3,5-triselenane,bis(3,4-epithio-1-tellurobutyl)tricycloselenaoctane,bis(3,4-epithio-1-tellurobutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-tellurobutyl)selenophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-telluropentyl)selenophane,2-(4,5-thioepoxy-2-telluropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-selenacyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1-selenacyclohexane, 2,3-, 2,4-,2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-selenacyclohexane, 2,3-, 2,5-or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-ditellurane, 2,3-, 2,5- or2,6-bis(4,5-epithio-2-telluropentyl)-1,4-ditellurane, 2,4-, 2,5- or5,6-bis(3,4-epithio-1-tellurobutyl)-1,3-ditellurane, 2,4-, 2,5- or5,6-bis(4,5-epithio-2-telluropentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6-or 3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-tellurane, 2,3-, 2,5-,2,6- or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-tellurane, 2,4- or4,5-bis(3,4-epithio-1-tellurobutyl)-1,3-ditellurolane, 2,4- or4,5-bis(4,5-epithio-2-telluropentyl)-1,3-ditellurolane, 2,4-, 2,5- or4,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or4,5-bis(4,5-epithio-2-telluropentyl)-1-thia-3-tellurolane,2,6-bis(4,5-epithio-2-telluropentyl)-1,3,5-tritellurane,bis(3,4-epithio-1-tellurobutyl)tricyclotelluraoctane,bis(3,4-epithio-1-tellurobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or3,4-bis(3,4-epithio-1-tellurobutyl)tellurophane, 2,3-, 2,4-, 2,5- or3,4-bis(4,5-epithio-2-telluropentyl)tellurophane,2-(4,5-thioepoxy-2-telluropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane,2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane, and 2,3-,2,4-, 2,5-, 2,6-, 3,4-, 3,5- or4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-telluracyclohexane;

E-3: Compounds Having Aromatic Backbone

1,3- or 1,4-bis(β-epithiopropyltelluro)benzene, 1,3- or1,4-bis(β-epithiopropyltelluromethyl)benzene,bis[4-(β-epithiopropyltelluro)phenyl]methane,2,2-bis[4-(β-epithiopropyltelluro)phenyl]propane,bis[4-(β-epithiopropyltelluro)phenyl] sulfide,bis[4-(β-epithiopropyltelluro)phenyl] sulfone, and4,4′-bis(β-epithiopropyltelluro)biphenyl; and

compounds obtained by replacing at least one hydrogen of theβ-epithiopropyl group in the above compounds with methyl.

The episulfide compounds (A) to (E) may include the organic compoundshaving an unsaturated group. Preferred examples thereof includevinylphenyl thioglycidyl ether, vinylbenzyl thioglycidyl ether,thioglycidyl methacrylate, thioglycidyl acrylate and allyl thioglycidylether.

Further, the other examples of the compounds having one epithio groupincludes sulfide compounds such as ethylene sulfide, propylene sulfide,and thioglycidol; thioglycidyl esters of mono carboxylic acid such asacetic acid, propionic acid, and benzoic acid; and thioglycidyl ethersuch as methyl thioglycidyl ether, ethyl thioglycidyl ether, propylthioglycidyl ether, and butyl thioglycidyl ether.

In the above, more preferred examples are the episulfide compounds (B),the episulfide compounds (C), and the episulfide compounds (D), and mostpreferred are the episulfide compounds (C) and the episulfide compounds(D) such as chain compounds, branched compounds, alicyclic compounds,aromatic compounds and hetero cyclic compounds having two or moreepithioethylthio group, epithioethylseleno group, β-epithiopropylthiogroup, β-epithiopropylseleno group as described above. Of the above,particularly preferred are chain compounds having two or moreepithioethylthio group, epithioethylseleno group, β-epithiopropylthiogroup and β-epithiopropylseleno group, such as bis(epithioethyl)sulfide, bis(epithioethyl) disulfide, bis(epithioethyl) selenide,bis(epithioethyl) diselenide, bis(β-epithiopropyl) sulfide,bis(β-epithiopropyl) disulfide, bis(β-epithiopropyl) selenide, andbis(β-epithiopropyl) diselenide.

Further, examples of the compound (a) include the episulfide compoundswith its episulfide group replaced by epoxy group.

The amine compound serving as the compound (b) includes the followingcompounds.

Compounds represented by the following Formula (2):R⁵ _(a)NH_(b)  (2)wherein R⁵ is an alkyl group having 1 to 8 carbon atoms; a is an integerfrom 1 to 3; b is an integer from 0 to 2; and a+b is 3.

Examples of the compounds of Formula (2) include methylamine,ethylamine, propylamine, butylamine, pentylamine, hexylamine,heptylamine, octylamine, dimethylamine, diethylamine dipropylamine,dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine,trimethylamine, triethylamine, tripropylamine, tributylamine,tripentylamine, trihexylamine, triheptylamine, and trioctylamine.

Compounds represented by the following Formula (3):R⁶(NH₂)c  (3)wherein R⁶ is a hydrocarbon group having 1 to 8 carbon atoms; and c isan integer from 2 to 4.

Examples of the compounds of Formula (3) include diaminomethane,diaminoethane, diaminopropane, diaminobutane, diaminopentane,diaminohexane, diaminoheptane, diaminooctane, triaminoethane,triaminopropane, triaminobutane, triaminopentane, triaminohexane,triaminoheptane, triaminooctane, tetraaminoethane, tetraaminopropane,tetraaminobutane, tetraaminopentane, tetraaminohexane,tetraaminoheptane, and tetraaminooctane.

Compounds represented by the following Formula (4):C-A_(d)  (4)wherein C is a mono- or divalent radical derived from a cycloalkanehaving 5 to 8 carbon atoms, a cycloalkene having 5 to 8 carbon atoms, acycloalkadiene having 5 to 8 carbon atoms, norbornane, norbornene,norbornadiene, tricyclodecane, tricyclodecene, tricyclodecadiene,pentacyclopentadecane, or pentacyclopentadecadiene; A is —NH₂ or—CH₂NH₂; d is 1 or 2; provided that C may be substituted by one or twomethyl or ethyl when A is —NH₂ and d is 2.

Examples of the compounds of Formula (4) include monoamino compoundssuch as aminocyclopentane, aminocyclopentene, aminocyclopentadiene,aminocyclohexane, aminocyclohexene, aminocyclohexadiene,aminocyclooctane, aminocyclooctene, aminocyclooctadiene,aminonorbornane, aminonorbornene, aminonorbornadiene,aminotricyclodecane, aminotricyclodecene, aminotricyclodecadiene,aminopentacyclopentadecane, and aminopentacyclopentadecadiene;mono(aminomethyl) compounds such as (aminomethyl)cyclopentane,(aminomethyl)cyclopentene, (aminomethyl)cyclopentadiene,(aminomethyl)cyclohexane, (aminomethyl)cyclohexene,(aminomethyl)cyclohexadiene, (aminomethyl)cyclooctane,(aminomethyl)cyclooctene, (aminomethyl)cyclooctadiene,(aminomethyl)norbornane, (aminomethyl)norbornene,(aminomethyl)norbornadiene, (aminomethyl)tricyclodecane,(aminomethyl)tricyclodecene, (aminomethyl)tricyclodecadiene,(aminomethyl)pentacyclopentadecane, and(aminomethyl)pentacyclopentadecadiene; diamino compounds such asdiaminocyclopentane, diaminocyclopentene, diaminocyclopentadiene,diaminocyclohexane, diaminocyclohexene, diaminocyclohexadiene,diaminocyclooctane, diaminocyclooctene, diaminocyclooctadiene,diaminonorbornane, diaminonorbornene, diaminonorbornadiene,diaminotricyclodecane, diaminotricyclodecene, diaminotricyclodecadiene,diaminopentacyclopentadecane, and diaminopentacyclopentadecadiene;bis(aminomethyl) compounds such as bis(aminomethyl)cyclopentane,bis(aminomethyl)cyclopentene, bis(aminomethyl)cyclopentadiene,bis(aminomethyl)cyclohexane, bis(aminomethyl)cyclohexene,bis(aminomethyl)cyclohexadiene, bis(aminomethyl)cyclooctane,bis(aminomethyl)cyclooctene, bis(aminomethyl)cyclooctadiene,bis(aminomethyl)norbornane, bis(aminomethyl)norbornene,bis(aminomethyl)norbornadiene, bis(aminomethyl)tricyclodecane,bis(aminomethyl)tricyclodecene, bis(aminomethyl)tricyclodecadiene,bis(aminomethyl)pentacyclopentadecane, andbis(aminomethyl)pentacyclopentadecadiene; diamino compounds having onemethyl group such as diaminomethylcyclopentane,diaminomethylcyclopentene, diaminomethylcyclopentadiene,diaminomethylcyclohexane, diaminomethylcyclohexene,diaminomethylcyclohexadiene, diaminomethylcyclooctane,diaminomethylcyclooctene, diaminomethylcyclooctadiene,diaminomethylnorbornane, diaminomethylnorbornene,diaminomethylnorbornadiene, diaminomethyltricyclodecane,diaminomethyltricyclodecene, diaminomethyltricyclodecadiene,diaminomethylpentacyclopentadecane, anddiaminomethylpentacyclopentadecadiene; diamino compounds having twomethyl groups such as diaminodimethylcyclopentane,diaminodimethylcyclopentene, diaminodimethylcyclopentadiene,diaminodimethylcyclohexane, diaminodimethylcyclohexene,diaminodimethylcyclohexadiene, diaminodimethylcyclooctane,diaminodimethylcyclooctene, diaminodimethylcyclooctadiene,diaminodimethylnorbornane, diaminodimethylnorbornene,diaminodimethylnorbornadiene, diaminodimethyltricyclodecane,diaminodimethyltricyclodecene, diaminodimethyltricyclodecadiene,diaminodimethylpentacyclopentadecane, anddiaminodimethylpentacyclopentadecadiene; diamino compounds having oneethyl group such as diaminoethylcyclopentane, diaminoethylcyclopentene,diaminoethylcyclopentadiene, diaminoethylcyclohexane,diaminoethylcyclohexene, diaminoethylcyclohexadiene,diaminoethylcyclooctane, diaminoethylcyclooctene,diaminoethylcyclooctadiene, diaminoethylnorbornane,diaminoethylnorbornene, diaminoethylnorbornadiene,diaminoethyltricyclodecane, diaminoethyltricyclodecene,diaminoethyltricyclodecadiene, diaminoethylpentacyclopentadecane, anddiaminoethylpentacyclopentadecadiene; and diamino compounds having twoethyl groups such as diaminodiethylcyclopentane,diaminodiethylcyclopentene, diaminodiethylcyclopentadiene,diaminodiethylcyclohexane, diaminodiethylcyclohexene,diaminodiethylcyclohexadiene, diaminodiethylcyclooctane,diaminodiethylcyclooctene, diaminodiethylcyclooctadiene,diaminodiethylnorbornane, diaminodiethylnorbornene,diaminodiethylnorbornadiene, diaminodiethyltricyclodecane,diaminodiethyltricyclodecene, diaminodiethyltricyclodecadiene,diaminodiethylpentacyclopentadecane, anddiaminodiethylpentacyclopentadecadiene.

Compounds represented by the following Formula (5):Ar-A_(e)  (5)wherein Ar is a radical derived from benzene, naphthalene, anthracene orphenanthrene; A is —NH₂ or —CH₂NH₂; and e is 1 or 2; provided that Armay be substituted by 1 to 4 substituents selected from methyl, ethyl,fluoro, chloro and bromo.

Examples of the compounds of Fourmula (5) include monoamino compoundssuch as aniline, aminonaphthalene, aminoanthracene, amino phenanthrene,aminotoluene, aminoxylene, aminofluorobenzene, aminofluoronaphthalene,aminofluorotoluene, aminofluoroxylene, aminochlorobenzene,aminochloronaphthalene, aminochlorotoluene, aminochloroxylene,aminobromobenzene, aminobromonaphthalene, aminobromotoluene, andaminobromoxylene; mono(aminomethyl) compounds such as(aminomethyl)benzene, (aminomethyl)naphthalene, (aminomethyl)toluene,(aminomethyl)xylene, (aminomethyl)fluorobenzene,(aminomethyl)fluoronaphthalene, (aminomethyl)fluorotoluene,(aminomethyl)fluoroxylene, (aminomethyl)chlorobenzene,(aminomethyl)chloronaphthalene, (aminomethyl)chlorotoluene,(aminomethyl)chloroxylene, (aminomethyl)bromobenzene,(aminomethyl)bromonaphthalene, (aminomethyl)bromotoluene, and(aminomethyl)bromoxylene; diamino compounds such as aminoaniline,diaminonaphthalene, diaminotoluene, diaminoxylene, diaminofluorobenzene,diaminofluoronaphthalene, diaminofluorotoluene, diaminofluoroxylene,diaminochlorobenzene, diaminochloronaphthalene, diaminochlorotoluene,diaminochloroxylene, diaminobromobenzene, diaminobromonaphthalene,diaminobromotoluene, diaminobromoxylene; bis(aminomethyl) compounds suchas bis(aminomethyl)benzene, bis(aminomethyl)naphthalene,bis(aminomethyl)toluene, bis(aminomethyl)xylene,bis(aminomethyl)fluorobenzene, bis(aminomethyl)fluoronaphthalene,bis(aminomethyl)fluorotoluene, bis(aminomethyl)fluoroxylene,bis(aminomethyl)chlorobenzene, bis(aminomethyl)chloronaphthalene,bis(aminomethyl)chlorotoluene, bis(aminomethyl)chloroxylene,bis(aminomethyl)bromobenzene, bis(aminomethyl)bromonaphthalene,bis(aminomethyl)bromotoluene, and bis(aminomethyl)bromoxylene; diaminocompounds having one methyl group such as diaminomethylnaphthalene,diaminomethylfluorobenzene, diaminomethylfluoronaphthalene,diaminomethylfluorotoluene, diaminomethylfluoroxylene,diaminomethylchlorobenzene, diaminomethylchloronaphthalene,diaminochlorotoluene, diaminomethylbromobenzene,diaminomethylbromonaphthalene, and diaminobromotoluene; diaminocompounds having two methyl groups such as aminodimethylaniline,diaminodimethylnaphthalene, diaminodimethylfluorobenzene,diaminodimethylfluoronaphthalene, diaminomethylfluorotoluene,diaminofluoroxylene, diaminodimethylchlorobenzene,diaminodimethylchloronaphthalene, diaminochloroxylene,diaminodimethylbromobenzene, diaminodimethylbromonaphthalene, anddiaminobromoxylene; diamino compounds having one ethyl group such asdiaminoethylbenzene, diaminoethylnaphthalene, diaminoethylfluorobenzene,diaminoethylfluoronaphthalene, diaminoethylfluorotoluene,diaminoethylfluoroxylene, diaminoethylchlorobenzene,diaminoethylchloronaphthalene, diaminoethylchlorobenzene,diaminoethylbromobenzene, diaminoethylbromonaphthalene, anddiaminoethylbromobenzene; diamino compounds having two ethyl groups suchas diaminodiethylbenzene, diaminodiethyltoluene, diaminodiethylxylene,diaminodiethylnaphthalene, diaminodiethylfluorobenzene,diaminodiethylfluoronaphthalene, diaminodiethylfluorotoluene,diaminodiethylfluorobenzene, diaminodiethylchlorobenzene,diaminodiethylchloronaphthalene, diaminodiethylchlorobenzene,diaminodiethylbromobenzene, diaminodiethylbromonaphthalene, anddiaminodiethylbromobenzene.

Compounds represented by the following Formula (6):

wherein R⁷ is phenylene group or cyclohexylene group which may besubstituted by 1 to 3 substituents selected from alkyl having 1 to 4carbon atoms, chloro, bromo and iodo.

Examples of the compounds of Formula (6) include compounds wherein R⁷ isphenylene such as methylene bis(aminobenzene), methylenebis(aminotoluene), methylene bis(aminoxylene), methylenebis(aminomethylethylbenzene), methylene bis(aminomethylpropylbenzene),methylene bis(aminomethylbutylbenzene), methylenebis(aminodiethylbenzene), methylene bis(aminoethylpropylbenzene),methylene bis(aminodipropylbenzene), methylenebis(aminopropylbutylbenzene), methylene bis(aminodibutylbenzene),methylene bis(aminochlorobenzene), methylene bis(aminochlorotoluene),methylene bis(aminochloroxylene), methylenebis(aminochloromethylethylbenzene), methylenebis(aminochloromethylpropylbenzene), methylenebis(aminochloromethylbutylbenzene), methylenebis(aminochlorodiethylbenzene), methylenebis(aminochloroethylpropylbenzene), methylenebis(aminochlorodipropylbenzene), methylenebis(aminochloropropylbutylbenzene), methylenebis(aminochlorodibutylbenzene), methylene bis(aminobromobenzene),methylene bis(aminobromotoluene), methylene bis(aminobromoxylene),methylene bis(aminobromomethylethylbenzene), methylenebis(aminobromomethylpropylbenzene), methylenebis(aminobromomethylbutylbenzene), methylenebis(aminobromodiethylbenzene), methylenebis(aminobromoethylpropylbenzene), methylenebis(aminobromodipropylbenzene), methylenebis(aminobromopropylbutylbenzene), methylenebis(aminobromodibutylbenzene), methylene bis(aminoiodobenzene),methylene bis(aminoiodotoluene), methylene bis(aminoiodoxylene),methylene bis(aminoiodomethylethylbenzene), methylenebis(aminoiodomethylpropylbenzene), methylenebis(aminoiodomethylbutylbenzene), methylenebis(aminoiododiethylbenzene), methylenebis(aminoiodoethylpropylbenzene), methylenebis(aminoiododipropylbenzene), methylenebis(aminoiodopropylbutylbenzene), and methylenebis(aminoiododibutylbenzene); and compounds wherein R⁷ is cyclohexylenesuch as methylene bis(aminocyclohexane), methylenebis(aminomethylcyclohexane), methylene bis(aminodimethylcyclohexane),methylene bis(aminomethylethylcyclohexane), methylenebis(aminomethylpropylcyclohexane), methylenebis(aminomethylbutylcyclohexane), methylenebis(aminodiethylcyclohexane), methylerie bis(aminoethylpropylcyclohexane), methylene bis(aminodipropylcyclohexane),methylene bis(aminopropylbutylcyclohexane), methylenebis(aminodibutylcyclohexane), methylene bis(aminochlorocyclohexane),methylene bis(aminochloromethylcyclohexane), methylenebis(aminochlorodimethylcyclohexane), methylenebis(aminochloromethylethylcyclohexane), methylenebis(aminochloromethylpropylcyclohexane), methylenebis(aminochloromethylbutylcyclohexane), methylenebis(aminochlorodiethylcyclohexane), methylenebis(aminochloroethylpropylcyclohexane), methylenebis(aminochlorodipropylcyclohexane), methylenebis(aminochloropropylbutylcyclohexane), methylenebis(aminochlorodibutylcyclohexane), methylenebis(aminobromocyclohexane), methylene bis(aminobromochlorocyclohexane),methylene bis(aminobromodimethylcyclohexane), methylenebis(aminobromomethylethylcyclohexane), methylenebis(aminobromomethylpropylcyclohexane), methylenebis(aminobromomethylbutylcyclohexane), methylenebis(aminobromodiethylcyclohexane), methylenebis(aminobromoethylpropylcyclohexane), methylenebis(aminobromodipropylcyclohexane), methylenebis(aminobromopropylbutylcyclohexane), methylenebis(aminobromodibutylcyclohexane), methylene bis(aminoiodocyclohexane),methylene bis(aminoiodotoluene), methylene bis(aminoiodoxylene),methylene bis(aminoiodomethylethylcyclohexane), methylenebis(aminoiodomethylpropylcyclohexane), methylenebis(aminoiodomethylbutylcyclohexane), methylenebis(aminoiododiethylcyclohexane), methylenebis(aminoiodoethylpropylcyclohexane), methylenebis(aminoiododipropylcyclohexane), methylenebis(aminoiodopropylbutylcyclohexane), and methylenebis(aminoiododibutylcyclohexane).

Compounds represented by the following Formula (7):B—R⁸—SH  (7)wherein R⁸ is phenylene group or cyclohexylene group; B is —NH₂ when R⁸is phenylene or B is —NH₂ or —R⁹NH₂ when R⁸ is cyclohexylene group; andR⁹ is alkylene group having 1 to 4 carbon atoms; provided that R⁸ may besubstituted by one or two alkyl groups having 1 to 4 carbon atoms.

Examples of the compounds of Formula (7) include compounds wherein R⁸ isphenylene such as aminobenzenethiol, aminomethylbenzenethiol,aminoethylbenzenethiol, aminopropylbenzenethiol, aminobutylbenzenethiol,aminodimethylbenzenethiol, aminodiethylbenzenethiol,aminodipropylbenzenethiol, aminodibutylbenzenethiol,aminoethylmethylbenzenethiol, aminopropylmethylbenzenethiol,aminobutylpropylbenzenethiol, aminoethylpropylbenzenethiol,aminoethylbutylbenzenethiol, and aminopropylbutylbenzenethiol; andcompounds wherein R⁸ is cyclohexylene such as aminomercaptocyclohexane,(aminomethyl) mercaptocyclohexane, (aminoethyl)mercaptocyclohexane,(aminopropyl)mercaptocyclohexane, (aminobutyl)mercaptocyclohexane,amino(dimethyl)mercaptocyclohexane, amino(diethyl)mercaptocyclohexane,amino(dipropyl)mercaptocyclohexane, amino(dibutyl)mercaptocyclohexane,amino (ethylmethyl)mercaptocyclohexane,amino(propylmethyl)mercaptocyclohexane, amino(butylpropyl)cyclohexane,amino(ethylpropyl)mercaptocyclohexane,amino(ethylbutyl)mercaptocyclohexane, andamino(propylbutyl)mercaptocyclohexane.

Also, (amino)(mercapto)-1,4-dithiane; amino(C₂-C₆ alkane)thiols such asaminoethanethiol, aminopropanethiol, aminobutanethiol,aminopentanethiol, and aminohexanethiol; aminomercaptopyridine;aminofurfurylmercaptane; aminomercaptothiazole; andaminomercaptotriazole are usable as the compounds (b).

The amine compound may contain a color tone stabilizer. The aminecompound may partly include a mercapto compound or may be anamino-terminated polymeric compound.

Preferred compounds (b) are the compounds having two or more aminogroups such as the compounds of Formula (3), the compounds of Formula(4) wherein d is 2, the compounds of Formula (5) wherein e is 2, and thecompounds of Formula (6); and the compounds of Formula (7).

More preferred compounds (b) are the compounds of Formula (5) wherein eis 2, the compounds of Formula (6) and the compounds of Formula (7),still more preferred compounds (b) are the compounds of Formula (5)wherein e is 2 and the compounds of Formula (7), and most preferredcompounds (b) are the compounds of Formula (7).

The isocyanate compound serving as the compound (c) includes anycompounds having in one molecule at least one isocyanate group and/orisothiocyanate group. Examples of the compounds (c) includes isocyanatecompounds such as methyl isocyanate, ethyl isocyanate, propylisocyanate, isopropyl isocyanate, n-butyl isocyanate, sec-butylisocyanate, tert-butyl isocyanate, pentyl isocyanate, hexyl isocyanate,octyl isocyanate, dodecyl isocyanate, cyclohexyl isocyanate, phenylisocyanate, tolyl isocyanate, diethylene diisocyanate, tetramethylenediisocyanate, hexamethylene diisocyanate, trimethylhexamethylenediisocyanate, cyclohexane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,2,6-bis(isocyanatomethyl)decahydronaphthalene, lysine triisocyanate,2,4-tolylenediisocyanate, 2,6-tolylene diisocyanate, o-tolydynediisocyanate, 4,4′-diphneylmethane diisocyanate, diphenyl etherdiisocyanate, 3-(2′-isocyanatecyclohexyl)propyl isocyanate,tris(phenylisocyanate) thiophosphate, isopropylidenebis(cyclohexylisocyanate), 2,2′-bis(4-isoisocyanatephenyl)propane,triphenylmethane triisocyanate, bis(diisocyanatetolyl)phenylmethane,4,4′,4″-triisocyanate-2,5-dimethoxyphenylamine,3,3′-dimethoxybenzidine-4,4′-diisocyanate, 1,3-phenylene diisocyanate,1,4-phenylene diisocyanate, 4,4′-diisocyanatobiphenyl,4,4′-diisocyanato-3,3′-dimethylbiphenyl,dicyclohexylmethane-4,4′-diisocyanate,1,1′-methylenebis(4-isocyanatobenzene),1,1′-methylenebis(3-methyl-4-isocyanatobenzene), m-xylylenediisocyanate, p-xylylene diisocyanate,1,3-bis(1-isocyanate-1-methylethyl)benzene,1,4-bis(1-isocyanate-1-methylethyl)benzene,1,3-bis(2-isocyanato-2-propyl)benzene,2,6-bis(isocyanatomethyl)naphthalene, 1,5-naphthalene diisocyanate,bis(isocyanatemethyl)tetrahydrodicyclopentadiene,bis(isocyanatemethyl)dicyclopentadiene,bis(isocyanatemethyl)tetrahydrothiophene,2,5-diisocyanatemethylnorbornene, bis(isocyanatemethyl)adamantane,dimeric acid diisocyanate, 1,3,5-tri(1-isoisocyanatehexyl)isocyanuricacid, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyldiisocyanate, bis[(4-isocyanatomethyl)phenyl] sulfide,2,5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl thiophene,dithiodiethyl diisocyanate, and dithiodipropyl diisocyanate; andcompounds derived from the above isocyanate compounds by replacing allor a part of the isocyanate group thereof with isothiocyanate group. Thepolyisocyanate compounds such as dimers produced by biuret reaction,cyclic trimers, alcohol adducts and thiol adducts are usable as thecompounds (c).

Another example of the isocyanate compounds as the compound (c) areNCO-terminated urethane prepolymers and NCO-terminated thiourethanepolymers derived from an active hydrogen compound and an isocyanatecompound.

Preferred examples of active hydrogen compounds for producingNCO-terminated urethane prepolymers and thiourethane prepolymers arepolyester polyol, polythioester polyol, polythioester polythiol,polycaprolactone polyol, polycaprolactone polythiol, polyether polyol,polyether polythiol, polythioether polyol, polythioether polythiol,polycarbonate polyol, polycarbonate polythiol, polyurethane polyol,polyurethane polythiol, polythiourethane polythiol,bis(7-mercapto-2,5-dithiaheptylphenyl) sulfide, and polymercaptocompound, each having molecular weight of 400 to 5000. The activehydrogen compound is preferably reacted with an isocyanate compound inan active hydrogen group/NCO group ratio of 1.0 to 5.0.

Preferred compound (c) are the compounds having two or more isocyanategroups. Examples of the isocyanate compounds are diethylenediisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate,trimethylhexamethylene diisocyanate, cyclohexane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,2,6-bis(isocyanatomethyl)decahydronaphthalene, lysine triisocyanate,2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, o-tolydynediisocyanate, 4,4′-diphneylmethane diisocyanate, diphenyl etherdiisocyanate, 3-(2′-isocyanatocyclohexyl)propyl isocyanate,tris(phenylisocyanate) thiophosphate, isopropylidenebis(cyclohexylisocyanate), 2,2′-bis(4-isoisocyanatophenyl)propane,triphenylmethane triisocyanate, bis(diisocyanatotolyl)phenylmethane,4,4′,4″-triisocyanato-2,5-dimethoxyphenylamine,3,3′-dimethoxybenzidine-4,4′-diisocyanate, 1,3-phenylene diisocyanate,1,4-phenylene diisocyanate, 4,4′-diisocyanatobiphenyl,4,4′-diisocyanato-3,3′-dimethylbiphenyl,dicyclohexylmethane-4,4′-diisocyanate,1,1′-methylenebis(4-isocyanatobenzene),1,1′-methylenebis(3-methyl-4-isocyanatobenzene), m-xylylenediisocyanate, p-xylylene diisocyanate,1,3-bis(1-isocyanato-1-methylethyl)benzene,1,4-bis(1-isocyanato-1-methylethyl)benzene,1,3-bis(2-isocyanato-2-propyl)benzene,2,6-bis(isocyanatomethyl)naphthalene, 1,5-naphthalene diisocyanate,bis(isocyanatomethyl)tetrahydrodicyclopentadiene,bis(isocyanatomethyl)dicyclopentadiene,bis(isocyanatomethyl)tetrahydrothiophene,2,5-diisocyanatomethylnorbornene, bis(isocyanatomethyl)adamantane,dimeric acid diisocyanate, 1,3,5-tri(1-isoisocyanatohexyl)isocyanuricacid, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyldiisocyanate, bis[(4-isocyanatomethyl)phenyl] sulfide,2,5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl-1,4-dithiane,2,5-diisocyanatomethyl thiophene, dithiodiethyl diisocyanate,dithiodipropyl diisocyanate, and the above compounds with its all orpart of isocyanate group replaced by isothiocyanate group. Examplesthereof also include NCO-biterminated urethane prepolymer andthiourethane prepolymer derived from an active hydrogen compound and anisocyanate compound.

Particularly preferred compound (c) aredicyclohexylmethan-4,4′-diisocyanate and NCO-biterminated urethane orthiourethane prepolymer derived from an active hydrogen compound and anisocyanate compound.

The compound (a), (b) and (c) are not limited to those mentioned aboveand may be used alone or in combination of two or more.

The composition of the present invention comprising the compound (a),compound (b), compound (c) is polymerized to a resin under heating inthe presence or absence of a curing catalyst, preferably in the presenceof a curing catalyst. The polymerization may be carried out by firstprepolymerizing the compound (a) with the compound (b), and then withthe compound (c), alternatively, by first prepolymerizing the compound(a) with the compound (c), and then with the compound (b). Any othercombinations of the compounds (a), (b) and (c) may be available forprepolymerization.

As the curing catalyst, usable are amines, phosphines, quaternaryammonium salts, quaternary phosphonium salts, tertiary sulfonium salts,secondary iodonium salts, mineral acids, Lewis acids, organic acids,silicic acids, tetrafluoroboric acids, peroxides, azo compounds,condensates of aldehyde and amine compound, guanidine compounds,thiourea compounds, thiazole compounds, sulfenamide compounds, thiuramcompounds, salts of dithiocarbamic acid, salts of xanthogenic acid, andesters of acid phosphoric acid. Examples of the curing catalysts arementioned below.

(1) Amines

primary amines such as ethylamine, n-propylamine, sec-propylamine,n-butylamine, sec-butylamine, isobutylamine, tert-butylamine,pentylamine, hexylamine, heptylamine, octylamine, decylamine,laurylamine, myristylamine, 1,2-dimethylhexylamine, 3-pentylamine,2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol,2-aminopropanol, aminobutanol, aminopentanol, aminohexanol,3-ethoxypropylamine, 3-propoxypropylamine, 3-isopropoxypropylamine,3-butoxypropylamine, 3-isobutoxypropylamine,3-(2-ethylhexyloxy)propylamine, aminocyclopentane, aminocyclohexane,aminonorbornene, aminomethylcyclohexane, aminobenzene, benzylamine,phenetylamine, α-phenylethylamine, naphthylamine and furfurylamine;

primary polyamines such as ethylenediamine, 1,2-diaminopropane,1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane,1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane,1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine,diethylaminopropylamine, bis-(3-aminopropyl) ether,1,2-bis-(3-aminopropoxy)ethane,1,3-bis-(3-aminopropoxy)-2,2′-dimethylpropane, aminoethylethanolamine,1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane,1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated4,4′-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine,N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine,N-aminopropylmorpholine, isophoronediamine, menthanediamine,1,4-bisaminopropylpiperadine, o-, m- or p-phenylenediamine, 2,4- or2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine,4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine,4-methoxy-6-methyl-m-phenylenediamine, m- or p-xylylenediamine, 1,5- or2,6-naphthalenediamine, benzidine, 4,4′-bis(o-toluidine), dianisidine,4,4′-diaminodiphenylmethane, 2,2-(4,4′-diaminodiphenyl)propane,4,4′-diaminodiphenyl ether, 4,4′-thiodianiline, 4,4′-diaminodiphenylsulfone, 4,4′-diaminoditolyl sulfone, methylenebis(o-chloroaniline),3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane,diethylenetriamine, iminobispropylamine, methyliminobispropylamine,bis(hexamethylene)triamine, triethylenetetramine,tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperadine,N-aminopropylpiperadine, 1,4-bis(aminoethylpiperadine),1,4-bis(aminopropylpiperadine), 2,6-diaminopyridine, andbis(3,4-diaminophenyl) sulfone;

secondary amines such as diethylamine, dipropylamine, di-n-butylamine,di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine,dihexylamine, dioctylamine, di(2-ethylhexyl)amine, methylhexylamine,diallylamine, pyrrolidine, piperidine, 2-, 3- or 4-picoline, 2,4-, 2,6-or 3,5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline,dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrol, indoline,indole, and morpholine;

secondary polyamines such as N,N′-dimethylethylenediamine,N,N′-dimethyl-1,2-diaminopropane, N,N′-dimethyl-1,3-diaminopropane,N,N′-dimethyl-1,2-diaminobutane, N,N′-dimethyl-1,3-diaminobutane,N,N′-dimethyl-1,4-diaminobutane, N,N′-dimethyl-1,5-diaminopentane,N,N′-dimethyl-1,6-diaminohexane, N,N′-dimethyl-1,7-diaminoheptane,N,N′-diethylethylenediamine, N,N′-diethyl-1,2-diaminopropane,N,N′-diethyl-1,3-diaminopropane, N,N′-diethyl-1,2-diaminobutane,N,N′-diethyl-1,3-diaminobutane, N,N′-diethyl-1,4-diaminobutane,N,N′-diethyl-1,6-diaminohexane, piperadine, 2-methylpiperadine, 2,5- or2,6-dimethylpiperadine, homopiperadine, 1,1-di(4-piperidyl)methane,1,2-di(4-piperidyl)ethane, 1,3-di(4-piperidyl)propane, and1,4-di(4-piperidyl)butane; tertiary amines such as trimethylamine,triethylamine, tri-n-propylamine, triisopropylamine,tri(1,2-dimethylpropyl)amine, tri(3-methoxypropyl)amine,tri-n-butylamine, triisobutylamine, tri-sec-butylamine,tri-n-pentylamine, tri-3-pentylamine, tri-n-hexylamine,tri-n-octylamine, tri(2-ethylhexyl)amine, tridodecylamine,trilaurylamine, dicyclohexylethylamine, cyclohexyldiethylamine,tricyclohexylamine, N,N-dimethylhexylamine, N-methyldihexylamine,N,N-dimethylcyclohexylamine, N-methyldicyclohexylamine,N,N-diethylethanolamine, N,N-dimethylethanolamine,N-ethyldiethanolamine, triethanolamine, tribenzylamine,N,N-dimethylbenzylamine, diethylbenzylamine, triphenylamine,N,N-dimethylamino-p-cresol, N,N-dimethylaminomethylphenol,2-(N,N-dimethylaminomethyl)phenol, N,N-dimethylaniline,N,N-diethylaniline, pyridine, quinoline, N-methylmorpholine,N-methylpiperidine, and2-(2-dimethylaminoethoxy)-4-methyl-1,3,2-dioxabornane;

tertiary polyamines such as tetramethylethylenediamine, pyrazine,N,N′-dimethylpiperadine, N,N′-bis(2-hydroxypropyl)piperadine,hexamethylenetetramine, N,N,N′,N′-tetramethyl-1,3-butaneamine,2-dimethylamino-2-hydroxypropane, diethyaminoethanol,N,N,N-tris(3-dimethylaminopropyl)amine,2,4,6-tris(N,N,-dimethylaminomethyl)phenol, and heptamethylisobiguanide;

imidazoles such as imidazole, N-methylimidazole, 2-methylimidazole,4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole,N-butylimidazole, 2-butylimidazole, N-undecylimidazole,2-undecylimidazole, N-phenylimidazole, 2-phenylimidazole,N-benzylimidazole, 2-benzylimidazole, 2-mercaptoimidazole,2-mercapto-N-methylimidazole, 2-mercaptobenzimidazole,3-mercapto-4-methyl-4H-1,2,4-triazole, 5-mercapto-1-methyl-tetrazole,2,5-dimercapto-1,3,4-thiadiazole, 1-benzyl-2-methylimidazole,N-(2′-cyanoethyl)-2-methylimidazole,N-(2′-cycanoethyl)-2-undecylimidazole,N-(2′-cyanoethyl)-2-phenylimidazole,3,3-bis-(2-ethyl-4-methylimidazolyl)methane, and addition products ofalkylimidazoles and isocyanuric acid; and

amidines such as 1,8-diazabicyclo[5.4.0]undecene-7,1,5-diazabicyclo[4.3.0]nonene-5, and6-dibutylamino-1,8-diazabicyclo[5.4.0]undecene-7.

(2) Complexes of Amines (1) and Borane or Boron Trifluoride

(3) Phosphines

trimethylphosphine, triethylphosphine, triisopropylphosphine,tri-n-butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine,tricyclohexylphosphine, triphenylphosphine, tribenzylphosphine,tris(2-methylphenyl)phosphine, tris(3-methylphenyl)phosphine,tris(4-methylphenyl)phosphine, tris(diethylamino)phosphine,tris(4-methylphenyl)phosphine, dimethylphenylphosphine,diethylphenylphosphine, dicyclohexylphenylphosphine,ethyldiphenylphosphine, diphenylcyclohexylphosphine, andchlorodiphenylphosphine.

(4) Quaternary Ammonium Salts

tetramethylammonium chloride, tetramethylammonium bromide,tetramethylammonium acetate, tetraethylammonium chloride,tetraethylammonium bromide, tetraethylammonium acetate,tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride,tetra-n-butylammonium bromide, tetra-n-butylammonium iodide,tetra-n-butylammonium acetate, tetra-n-butylammonium borohydride,tetra-n-butylammonium hexafluorophosphite, tetra-n-butylammoniumhydrogensulfite, tetra-n-butylammonium tetrafluoroborate,tetra-n-butylammonium tetraphenylborate, tetra-n-butylammoniump-toluenesulfonate, tetra-n-hexylammonium chloride,tetra-n-hexylammonium bromide, tetra-n-hexylammonium acetate,tetra-n-octylammonium chloride, tetra-n-octylammonium bromide,tetra-n-octylammonium acetate, trimethyl-n-octylammonium chloride,trimethyldecylammonium chloride, trimethyldodecylammonium chloride,trimethylcetylammonium chloride, trimethyllaurylammonium chloride,trimethylbenzylammonium chloride, trimethylbenzylammonium bromide,triethyl-n-octylammonium chloride, triethylbenzylammonium chloride,triethylbenzylammonium bromide, tri-n-butyl-n-octylammonium chloride,tri-n-butylbenzylammonium fluoride, tri-n-butylbenzylammonium chloride,tri-n-butylbenzylammonium bromide, tri-n-butylbenzylammonium iodide,n-butyldimethylbenzylammonium chloride, n-octyldimethylbenzylammoniumchloride, decyidimethylbenzylammonium chloride,dodecyldimethylbenzylammonium chloride, cetyldimethylbenzylammoniumchloride, lauryldimethylbenzylammonium chloride, methyltriphenylammoniumchloride, methyltribenzylammonium chloride, methyltriphenylammoniumbromide, methyltribenzylammonium bromide, ethyltriphenylammoniumchloride, ethyltribenzylammonium chloride, ethyltriphenylammoniumbromide, ethyltribenzylammonium bromide, n-butyltriphenylammoniumchloride, n-butyltribenzylammonium chloride, n-butyltriphenylammoniumbromide, n-butyltribenzylammonium bromide, 1-methylpyridinium chloride,1-methylpyridinium bromide, 1-ethylpyridinium chloride,1-ethylpyridinium bromide, 1-n-butylpyridinium chloride,1-n-butylpyridinium bromide, 1-n-hexylpyridinium chloride,1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide,1-n-dodecylpyridinium chloride, 1-n-dodecylpyridinium bromide,1-n-cetylpyridinium chloride, 1-n-cetylpyridinium bromide,1-phenylpyridinium chloride, 1-phenylpyridinium bromide,1-benzylpyridinium chloride, 1-benzylpyridinium bromide,1-methylpicolinium chloride, 1-methylpicolinium bromide,1-ethylpicolinium chloride, 1-ethylpicolinium bromide,1-n-butylpicolinium chloride, 1-n-butylpicolinium bromide,1-n-hexylpicolinium chloride, 1-n-hexylpicolinium bromide,1-n-octylpicolinium chloride, 1-n-octylpicolinium bromide,1-n-dodecylpicolinium chloride, 1-n-dodecylpicolinium bromide,1-n-cetylpicolinium chloride, 1-n-cetylpicolinium bromide,1-phenylpicolinium chloride, 1-phenylpicolinium bromide,1-benzylpicolinium chloride, and 1-benzylpicolinium bromide.

(5) Quaternary Phosphonium Salts

tetramethylphosphonium chloride, tetramethylphosphonium bromide,tetraethylphosphonium chloride, tetraethylphosphonium bromide,tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide,tetra-n-butylphosphonium iodide, tetra-n-hexylphosphonium bromide,tetra-n-octylphosphonium bromide, methyltriphenylphosphonium bromide,methyltriphenylphosphonium iodide, ethyltriphenylphosphonium bromide,ethyltriphenylphosphonium iodide, n-butyltriphenylphosphonium bromide,n-butyltriphenylphosphonium iodide, n-hexyltriphenylphosphonium bromide,n-octyltriphenylphosphonium bromide, tetraphenylphosphonium bromide,tetrakishydroxymethylphosphonium chloride,tetrakishydroxymethylphosphonium bromide,tetrakishydroxyethylphosphonium chloride, andtetrakishydroxybutylphosphonium chloride.

(6) Tertiary Sulfonium Salts

trimethylsulfonium bromide, triethylsulfonium bromide,tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide,tri-n-butylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate,tri-n-hex ylsulfonium bromide, tri-n-octylsulfonium bromide,triphenylsulfonium chloride, triphenylsulfonium bromide, andtriphenylsulfonium iodide.

(7) Secondary Iodonium Salts

diphenyliodonium chloride, diphenyliodonium bromide, anddiphenyliodonium iodide.

(8) Mineral Acids

hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid andcarbonic acid, and half-esters of the mineral acids.

(9) Lewis Acids

boron trifluoride, boron trifluoride etherate, aluminum fluoride,aluminum chloride, triphenylaluminum, potassium octanoate, calciumacetate, tetraisopropoxytitanium, tetrabutoxytitanium,tetrachlorotitanium, 2-ethylhexyl titanate, dimethyltin oxide,dimethyltin dichloride, dibutyltin diacetate, dibutyltin acetate,dibutyltin dilaurate, dibutyltin laurate, dibutyltin octanoate,dibutyltin bis(dodecylmercaptide), dibutyltinbis(isooctylthioglycolate), dibutyltin oxide, butyltin trichloride,dibutyltin dichloride, tributyltin chloride, tetrabutyltin, dioctyltindiacetate, dioctyltin acetate, dioctyltin dilaurate, dioctyltin laurate,dioctyltin diricinolate, dioctyltin dioleate, dioctyltindi(6-hydroxy)caproate, dioctyltin bis(isooctylthoglycolate), dioctyltinoxide, dioctyltin dichloride, dioctyltin maleate, dioctyltinbis(butylmaleate), didodecyltin diricinolate, tin stearate, zincchloride, zinc acetylacetonato, copper oleate, copper acetylacetonato,iron acetylacetonato, iron naphthenate, iron lactate, iron citrate, andiron gluconate.

(10) Organic Acids and their Semi Esters.

(11) Silicic Acid and Tetrafluoroboric Acid.

(12) Peroxides

cumyl peroxyneodecanoate, diisopropyl peroxydicarbonate, diallylperoxydicarbonate, di-n-propyl peroxydicarbonate, dimyristylperoxydicarbonate, cumyl peroxyneohexanoate, t-hexyl peroxyneodecanoate,t-butyl peroxyneodecanoate, t-hexyl peroxyneohexanoate, t-butylperoxyneohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide,dicumyl peroxide, di-t-butyl peroxide, cumene hydroperoxide, andtert-butyl hydroperoxide.

(13) Azo Compounds

2,2′-Azobis(4-methoxy-2,4-dimethylvaleronitrile),2,2′-azobis(2-cyclopropylpropionitrile),2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobisisobutylonitrile,2,2′-azobis(2-methylbutylonitrile),1,1′-azobis(cyclohexane-1-carbonitrile),1-[(1-cyano-1-methyl)azo]formamide,2-pneylazo-4-methoxy-2,4-dimethylvaleronitrile,2,2′-azobis(2-methylpropane), and 2,2′-azobis(2,4,4-trimethylpentane).

(14) Condensates of Aldehyde and Amine Compound

reaction product of acetaldehyde and ammonia, condensate of formaldehydeand p-toluidine, condensate of acetaldehyde and p-toluidine, reactionproduct of formaldehyde and aniline, reaction product of acetaldehydeand aniline, reaction product of butylaldehyde and aniline, reactionproduct of formaldehyde, acetaldehyde and aniline, reaction product ofacetaldehyde, butylaldehyde and aniline, condensate of butylaldehyde andmonobutylamine, reaction product of butylaldehyde and butylideneaniline,reaction product of heptaldehyde and aniline, reaction product oftrichlotonylidenetetramine, condensate of α-ethyl-β-propylacrolein andaniline, and condensate of formaldehyde and alkylimidazole.

(15) Guanidine Compounds

diphenylguanidine, phenyltolylguanidine, phenylxylylguanidine,tolylxylylguanidine, di-o-tolylguanidine, o-tolylguanide,diphenylguanidine phthalate, tetramethylguanidine, anddi-o-tolylguanidine salt of dicatechol boric acid.

(16) Thiourea Compounds

thiocarboanilide, di-o-tolylthiourea, ethylenethiourea, diethylthiourea,dibutylthiourea, dilaurylthiourea, trimethylthiourea,dimethylethylthiourea, and tetramethylthiourea.

(17) Thiazole Compounds

2-mercaptobenzothiazole, dibenzothiazyl disulfide, cyclohexylamine saltof 2-mercaptobenzothiazole, 2-(2,4-dinitrophenylthio)benzothiazole,2-(morpholinodithio)benzothiazole,2-(2,6-dimethyl-4-morpholinodithio)benzothiazole,N,N-diethylthiocarbamoyl-2-benzothiazolyl disulfide,1,3-bis(2-benzothiazolylmercaptomethyl)urea, benzothiadiazylthiobenzoate, 2-mercaptothiazoline, sodium salt of 2-mercaptobenzothiazole,zinc salt of 2-mercaptobenzothiazole, and complex of dibenzothiazyldisulfide and zinc chloride.

(18) Sulfenamide Compounds

N-cyclohexyl-2-benzothiazyl sulfenamide, N-t-butyl-2-benzothiazylsulfenamide, N-t-oxtyl-2-benzothiazyl sulfenamide,N-oxydiethylene-2-benzothiazyl sulfenamide, N,N-diethyl-2-benzothiazylsulfenamide, N,N-diisopropyl-2-benzothiazyl sulfenamide, andN,N-dicyclohexyl-2-benzothiazyl sulfenamide.

(19) Thiuram Compounds

tetramethylthiuram monosulfide, tetraethylthiuram monosulfide,tetrabutylthiuram monosulfide, dipentamethylenethiuram monosulfide,tetramethylthiuram disulfide, tetraethylthiuram disulfide,tetrabutylthiuram disulfide, N,N′-dimethyl-N,N′-diphenylthiuramdisulfide, N,N′-diethyl-N,N′-diphenylthiuram disulfide,dipentamethylenethiuram disulfide, dipentamethylenethiuram tetrasulfide,and cyclic thiuram.

(20) Salts of Dithiocarbamic Acid

sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate, sodiumdibutyldithiocarbamate, sodium pentamethylenedithiocarbamate, sodiumcyclohexylethyldithiocarbamate, potassium dimethyldithiocarbamate, leaddimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincdiethyldithiocarbamate, zinc dibutyldithiocarbamate, zincdibenzyldithiocarbamate, zinc pentamethylenedithiocarbamate, zincdimethylpentamethylenedithiocarbamate, zinc ethylphenyldithiocarbamate,bismuth dimethyldithiocarbamate, cadmium diethyldithiocarbamate, cadmiumpentamethylenedithiocarbamate, selenium dimethyldithiocarbamate,selenium diethyldithiocarbamate, tellurium dimethyldithiocarbamate,tellurium diethyldithiocarbamate, iron dimethyldithiocarbamate, copperdimethyldithiocarbamate, diethylammonium diethyldithiocarbamate,N,N-dicyclohexylammonium dibutyldithiocarbamate, piperidiniumpentamethylenedithiocarbamate, cyclohexylethylammonium sodiumcyclohexylethyldithiocarbamate, pipecoliniummethylpentamethylenedithiocarbamate, and complex of zincpentamethylenedithiocarbamate and piperidine.

(21) Salts of Xanthogenic Acid

sodium isopropylxanthate, zinc isopropylxanthate, zinc butylxanthate,and disulfide dibutylxanthate.

(22) Esters of Acid Phosphoric Acid

mono- or dimethyl phosphate, mono- or diethyl phosphate, mono- ordipropyl phosphate, mono- or dibutyl phosphate, mono- or dihexylphosphate, mono- or dioctyl phosphate, mono- or didecyl phosphate, mono-or didodecyl phosphate, mono- or diphenyl phosphate, mono- or dibenzylphosphate, and mono- or didecanol phosphate.

The compounds recited above are examples of the polymerization catalystsfor polymerization curing the composition for optical materials of thepresent invention. However, the catalyst is not limited thereto as faras the compound is effective for curing the composition bypolymerization. These catalysts may be used alone or in combination oftwo or more. The addition amount of the catalyst is 0.0001 to 10.0 partsby weight, preferably 0.0005 to 5.0 parts by weight based on 100 partsby weight of the composition for optical materials. An amount of thecuring catalysts more than 10.0 parts by weight may reduce therefractive index and the heat resistance, discolor the cured product andpresent dangers of polymerization with violence.

The composition for optical materials of the present invention may becured by polymerization in the presence of a compound reactable withpart or all of the compounds (a) to (c) as a property improving additiveto improve the oxidation resistance, weatherability, dyeability,strength, impact resistance and refractive index. A catalyst forpolymerization curing may be added to the composition for the reactionwith the property improving additive, if desired. Examples of theproperty improving additives are phenol compounds, alcohol compounds,carboxylic acids, carboxylic anhydrides, vinyl compounds including(meta)acrylates, (thio)epoxy compounds, monofunctionally terminatedpolybutenes, compounds having a mercapto group, inorganic compoundshaving a sulfur atom, and inorganic compounds having a selenium atom.These compounds may be added as much as necessary for obtaining therequired properties as far as no adverse effect is produced.

To improve the practical properties of the optical materials beingproduced by polymerization-curing the composition of the presentinvention, the composition may be added with known additives such asantioxidants, ultraviolet light absorbents, anti-yellowing agents,bluing agents, color stabilizers and pigments. When the composition ofthe present invention is easy to separate from molds duringpolymerization, it is effective to use or add known external and/orinternal adhesion improvers, thereby controlling and improving theadhesion between the cured material being formed and the mold. On theother hand, when the composition of the present invention is difficultto release from molds after the polymerization, it is effective to useor add a known external or internal mold release agent, therebyimproving the releasability of the cured material being formed from themolds.

In the present invention, the main components (the compositioncontaining the compounds (a), (b), and (c)) is uniformly mixed with thesecondary components (catalyst, property improving additives, theadditives such as the adhesion or mold release improver, antioxidants,ultraviolet absorbers, anti-yellowing agents, bluing agents, colorstabilizers, and pigments). The resultant uniform mixture is cast into amold made of glass or metal, cured by polymerization under heating, andthen released from the mold to obtain the optical material.

The compounds (a), (b) and (c), property improving additives, catalystand additives may be all blended simultaneously in the same container,or may be blended by adding each component stepwise. Alternatively, afew of the components are blended in separate containers and thenblended together in the same container. The blending is carried out in amagnetic stirring mixer, a blade mixer, a kneader, a laboplastomill, astatic mixer, a V-shape mixer or a RIM mixing head.

The mixing temperature and time are not critical as far as thecomponents are sufficiently mixed. An excessively high temperature andan excessively long mixing time unfavorably make the casting operationdifficult because undesirable reaction between the essential componentsand the optional components is induced to increase the viscosity. Themixing temperature is about −50 to 150° C., preferably −30 to 140° C.,more preferably −5 to 140° C. The mixing time is 0.05 min to 24 h,preferably 0.1 s to 10 h, more preferably 1 s to 6 h.

The compound (a), the compound (b) the compound (c) and propertyimproving additives may be all or partly prepolymerized in the presenceor absence of the catalyst with or without stirring at −100 to 160° C.for 0.1 to 480 h, and then mixed with the secondary components. Theprepolymerization is preferably conducted at −10 to 120° C. for 0.1 to240 h, more preferably, at 0 to 100° C. for 0.1 to 120 h. Theprepolymerization may be carried out, if necessary, in the presence ofadditives such as the adhesion or mold release improvers, antioxidants,ultraviolet absorbers, anti-yellowing agents, bluing agents, colorstabilizers, and pigments.

The mixing of the pre-reacted main components with the secondarycomponents is carried out in the same condition as above.

The degasification under reduced pressure prior to the mixing, duringthe mixing or after the mixing of the main components and the secondarycomponents is preferred to prevent the generation of bubbles during thesubsequent casting step and curing step by polymerization. The degree ofevacuation is about 0.1 to 700 mmHg, preferably 0.5 to 300 mmHg. Toincrease the quality of the optical material of the invention, it ispreferred to remove impurities by filtering the composition or the mainor secondary components through a filter having a pore size of about0.05 to 3 μm.

After casting the starting mixture into a glass or metal mold, thecuring by polymerization is conducted using an electric furnace, a waterbath or an oil bath. When casting into a glass or metal mold, thestarting mixture may be cast into a mold from a mixer directly orthrough a syringe, a compression molding machine, an RIM molding machineor an injection molding machine. The curing time is 0.1 to 100 h,preferably 1 to 72 h. The curing temperature is −10 to 160° C.,preferably 0 to 140° C. The polymerization is carried out by keeping thestarting mixture at a given polymerization temperature for a givenperiod of time while raising the temperature at 0.1 to 100° C./h,lowering the temperature at 0.1 to 100° C./h or using a combinationthereof. After curing, it is preferred to anneal the optical material at50 to 150° C. for 10 min to 5 h because the strain of the opticalmaterial can be removed. Where necessary, the obtained optical materialmay be subjected to surface treatments for dyeing, hard coat formation,reflection prevention and clouding prevention.

The optical materials produced by the manners described above have ahigh impact resistance enough to prevent the rupture by the iron ball of500 g or more dropped from the height of 127 cm, a refractive index of1.55 to 1.75 and an Abbe's number of 35 to 55.

The present invention will be described in more detail by reference tothe following examples which should not be construed to limit the scopeof the invention thereto. The evaluation of cured products was carriedout in the following manners.

(1) Refractive Index (nD) and Abbe's Number (vD):

Measured at 25° C. using Abbe refractometer.

(2) Impact Resistance:

Iron balls of 500 g and 1000 g were dropped to a flat plate having athickness of 2.5 mm from the height of 127 cm. The plate not broken wasrated “good” and the plate broken was rated “poor”.

EXAMPLE 1

A mixture consisting of 60 parts by weight of bis(β-epithiopropyl)sulfide, 20 parts by weight of 4,4′-methylenebis(cyclohexyl isocyanate)and 20 parts by weight of diethyltoluenediamine was deaerated, cast intoa mold for flat lens of 2.5 mm thick and cured by polymerization in anoven by raising the temperature from 50° C. to 130° C. over 24 h toprepare a lens. The obtained lens was excellent in heat resistance andphysical properties, and showed an excellent transparency and surfacecondition. The refractive index, the Abbe's number and the impactresistance are shown in Table 1.

EXAMPLE 2

In nitrogen atmosphere, 33 parts by weight of polyesterglycol having anaverage molecular weight of 1000 prepared from adipic acid and1,6-hexanediol was reacted with 26 parts by weight of4,4′-methylenebis(cyclohexyl isocyanate) at 130° C. for one hour toprepare an isocyanate-terminated polyurethane prepolymer, to which 30parts by weight of bis(β-epithiopropyl) sulfide, 11 parts by weight ofdiethyltoluenediamine, 0.1 part by weight of tetrabutylphosphoniumbromide and 0.02 part by weight of di-n-butyltin dilaurate were added at70° C. under stirring. The resultant mixture was deaerated, cast into amold for flat lens of 2.5 mm thick and cured by polymerization in anoven by raising the temperature from 50° C. to 130° C. over 24 h toprepare a lens. The prepared lens was excellent in heat resistance andphysical properties, and showed an excellent transparency and surfacecondition. The refractive index, the Abbe's number and the impactresistance of the obtained lens are shown in Table 1.

EXAMPLES 3-10

The procedure of Example 2 was repeated except for using the chemicalcomposition shown in Table 1. In any of the examples, the prepared lenswas excellent in heat resistance and physical properties, and showed anexcellent transparency and surface condition. The refractive index, theAbbe's number and the impact resistance of the obtained lens are shownin Table 1.

TABLE 1 Evaluation Result Impact Chemical Composition (by weight)Resistance Ex. (a) (b) (c) others nD νD 500 g 1000 g 1 BES(60) DETDA(20)H12MDI(20) 1.63 37 Good Poor 2 BES(30) DETDA(11) A(59) 1.58 44 Good Good3 BES(15) DETDA(14) B(71) 1.58 39 Good Good 4 BES(15) DETDA(13) B(66)DMDS(6) 1.59 38 Good Good 5 BES(20) DETDA(3) B(66) DMDS(11) 1.60 38 GoodGood 6 BES(13) DETDA(14) B(68) S(2) 1.58 38 Good Good 7 BES(15)DETDA(14) C(71) 1.63 37 Good Good 8 BEDS(30) AET(5) A(65) 1.58 45 GoodGood 9 BEDS(30) ABT(9) B(61) 1.62 37 Good Good 10 BEDS(41) ABT(7) C(52)1.67 35 Good Good Note: 1. In Examples 1 to 10, 0.1 part by weight oftetrabutylphosphonium bromide and 0.02 part by weight of di-n-butyltindilaurate were added. 2. Compound (a) BES: bis(β-epithiopropyl) sulfideBEDS: bis(β-epithiopropyl) disulfide 3. Compound (b) DETDA:diethyltoluenediamine AET: aminoethanethiol ABT: aminobenzenethiol 4.Compound (c) H12MDI: 4,4′-methylene bis(cyclohexyl isocyanate) A:isocyanate-terminated polyurethane prepolymer prepared by reacting PEG(polyester glycol having an average molecular weight of 1000 derivedfrom adipic acid and 1,6-hexanediol) and H12MDI in a weight ratio of56/44 (OH/NCO = 1/3). B: isocyanate-terminated polythiourethaneprepolymer prepared by reacting the active hydrogen compound I(thiol-biterminated polythiourethane compound having a molecular weightof 1000 derived from di(mercaptoethyl) sulfide and hexamethylenediisocyanate) and H12MDI in a weight ratio of 56/44 (SH/NCO = 1/3). C:isocyanate-terminated polythiourethane prepolymer prepared by reactingthe active hydrogen compound II (HS—(CH₂—S—)₂₁—SH) and H12MDI in aweight ratio of 56/44 (SH/NCO = 1/3). 5. Others DMDS: di(mercaptoethyl)sulfide S: Sulfur

COMPARATIVE EXAMPLE 1

A bisphenol A polycarbonate having an average molecular weight of 50000was injection-molded into a flat plate of 2.5 mm thick. The refractiveindex, the Abbe's number and the impact resistance are shown in Table 2.The refractive index and Abbe's number of Comparative Example 1 werelower than those of Examples, and optical distortion was caused.

COMPARATIVE EXAMPLE 2

In nitrogen atmosphere, 100 parts by weight of bis(β-epithiopropyl)sulfide was mixed with 0.1 part by weight of tetrabutylphosphoniumbromide under stirring. After deaerated, the mixture was cast into amold for flat lens of 2.5 mm thick and cured by polymerization in anoven by raising the temperature from 30° C. to 100° C. over 20 h toprepare a lens. The prepared lens was excellent in heat resistance andphysical properties, and shown an excellent transparency and surfacecondition. The refractive index, the Abbe's number and the impactresistance of the obtained lens are shown in Table 2. As compared withthe Examples, the impact resistance was poor.

COMPARATIVE EXAMPLE 3

In nitrogen atmosphere, 36 parts by weight of2,5-dimercaptomethyl-1,4-dithiane (DMMD), 18 parts by weight ofpentaerythritol tetrakismercaptopropionate (PETMP), 46 parts by weightof 1,3-bis(isocyanatemethyl)cyclohexane (H6-XDI) and 0.01 part by weightof dimethyltin dichloride (DMTDCl) were mixed under stirring. Afterdeaerated, the mixture was cast into a mold for flat lens of 2.5 mmthick and polymerized by heating in an oven at 50° C. for 10 h, at 60°C. for 5 h, and then at 120° C. for 3 h to prepare a lens. The preparedlens was excellent in heat resistance and physical properties, andshowed an excellent transparency and surface condition. The refractiveindex, the Abbe's number and the impact resistance of the obtained lensare shown in Table 2. As compared with Examples, the impact resistancewas poor.

TABLE 2 Chemical Impact Composition Resistance Com. Ex. (by weight) nDνD 500 g 1000 g 1 PC(100) 1.58 29 Good Good 2 BES(99.9) 1.70 36 PoorPoor TBPB(0.1) 3 DMMD(36) 1.60 40 Poor Poor PETMP(18) H6-XDI(46)DMTDCl(0.01) Note: PC: bisphenol A polycarbonate having an averagemolecular weight of 50000 BES: bis(β-epithiopropyl) sulfide TBPB:tetrabutylphosphonium bromide DMMD: 2,5-dimercaptomethyl-1,4-dithianePETMP: pentaerythritol tetrakismercaptopropionate H6-XDI:1,3-bis(isocyanatemethyl)cyclohexane DMTDCl: dimethyltin dichloride

INDUSTRIAL APPLICABILITY

By curing the composition of the present invention by polymerization, aconventionally unknown optical material that has a higher strength ascompared with polycarbonates and is balanced in the refractive index andthe Abbe's number each higher than achieved by polycarbonates can beobtained.

1. A composition for optical materials comprising: a compound having inone molecule at least one structure represented by the following formula(1):

wherein R¹ is a single bond or a C₁-C₁₀ hydrocarbon group; each of R²,R³ and R⁴ is a C₁-C₁₀ hydrocarbon group or hydrogen; X is S, O, Se orTe; Y is S, O, Se or Te; and n is an integer from 0 to 5; an aminecompound; and an isocyanate-terminated urethane or thiourethaneprepolymer.
 2. The composition for optical materials according to claim1, wherein the amine compound is at least one compound selected from thegroup consisting of: compounds represented by the following formula (2):R⁵ _(a)NH_(b)  (2) wherein R⁵ is a hydrocarbon group having 1 to 8carbon atoms; a is an integer from 1 to 3; b is an integer from 0 to 2;and a+b is 3; compounds represented by the following formula (3):R⁶(NH₂)_(c)  (3) wherein R⁶ is a hydrocarbon group having 1 to 8 carbonatoms; and c is an integer from 2 to 4; compounds represented by thefollowing formula (4):C-A_(d)  (4) wherein C is a mono- or divalent radical derived from acycloalkane having 5 to 8 carbon atoms, a cycloalkene having 5 to 8carbon atoms, a cycloalkadiene having 5 to 8 carbon atoms, norbornane,norbornene, norbornadiene, tricyclodecane, tricyclodecene,tricyclodecadiene, pentacyclopentadecane, or pentacyclopentadecadiene; Ais —NH₂ or —CH₂NH₂; d is 1 or 2; provided that C may be substituted byone or two methyl or ethyl when A is —NH₂ and d is 2; compoundsrepresented by the following formula (5):Ar-A_(e)  (5) wherein Ar is a radical derived from benzene, naphthalene,anthracene or phenanthrene; A is —NH₂ or —CH₂NH₂; and e is 1 or 2;provided that Ar may be substituted by 1 to 4 substituents selected frommethyl, ethyl, fluoro, chloro and bromo; compounds represented by thefollowing formula (6):

wherein R⁷ is phenylene group or cyclohexylene group which may besubstituted by 1 to 3 substituents selected from alkyl having 1 to 4carbon atoms, chloro, bromo and iodo; compounds represented by thefollowing formula (7):  B—R⁸—SH  (7) wherein R⁸ is phenylene group orcyclohexylene group; B is —NH₂ when R⁸ is phenylene or B is —NH₂ or—R⁹NH₂ when R⁸ is cyclohexylene group; and R⁹ is alkylene group having 1to 4 carbon atoms; provided that R⁸ may be substituted by one or twoalkyl groups having 1 to 4 carbon atoms; (amino)(mercapto)-1,4-dithiane;amino(C₂-C₆ alkane)thiols; aminomercaptopyridine;aminofurfurylmercaptane; aminomercaptothiazole; andaminomercaptotriazole.
 3. The composition for optical materialsaccording to claim 2, wherein the amine compound has two or more aminogroups.
 4. The composition for optical materials according to claim 3,wherein the isocyanate-terminated urethane or thiourethane prepolymerhas two or more isocyanate groups.
 5. The composition for opticalmaterials according to claim 4, comprising 0.5 to 90 parts by weight ofthe compound of Formula 1, 1 to 40 parts by weight of the amine compoundand 10 to 90 parts by weight of the isocyanate-terminated urethane orthiourethane prepolymer.
 6. A method for producing an optical materialby curing the composition as defined in claim 5 by polymerization.
 7. Anoptical material produced by the method according to claim
 6. 8. Anoptical lens comprising the optical material according to claim
 7. 9.The composition for optical materials according to claim 1, wherein theamine compound has two or more amino groups.
 10. The composition foroptical materials according to claim 1, wherein theisocyanate-terminated urethane or thiourethane prepolymer has two ormore isocyanate groups.
 11. The composition for optical materialsaccording to claim 1, comprising 0.5 to 90 parts by weight of thecompound of Formula 1, 1 to 40 parts by weight of the amine compound and10 to 90 parts by weight of the isocyanate-terminated urethane orthiourethane prepolymer.
 12. A method for producing an optical materialby curing the composition as defined in claim 1 by polymerization. 13.An optical material produced by the method according to claim
 12. 14. Anoptical lens comprising the optical material according to claim
 13. 15.The composition for optical materials according to claim 1, wherein saidisocyanate-terminated urethane or thiourethane prepolymer is a reactionproduct of an active hydrogen compound and an isocyanate compound. 16.The composition for optical materials according to claim 15, whereinsaid active hydrogen compound is selected from the group consisting ofpolyester polyol, polythioester polyol, polythioester, polythiol,polycaprolactone polyol, polycaprolactone polythiol, polyether polyol,polyether polythiol, polythioether polyol, polythioether polythiol,polycarbonate polyol, polycarbonate polythiol, polyurethane polyol,polyurethane polythiol, polythiourethane polythiol,bis(7-mercapto-2,5-dithiaheptylphenyl) sulfide, and polymercaptocompound, each having a molecular weight of 400 to 5000.